Category: 7699-18-5

Reference of 7699-18-5, A common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The appropriate compound 2 (10 mmol) was dissolved inmethanol (100 mL) and treated with the equivalent of the appropriatealdehyde 1 and piperidine (1 mL). For compounds 39, 41 and42 the yield was much lower (5%), and an improvement (15-20%)was obtained by replacing piperidine with 33% NH4OHThe reaction mixture was refluxed for 5-10 h, except for compounds39-42 which required a longer reflux time (16-24 h; theprogress of the reaction was followed by TLC). The precipitate,formed on cooling, was collected by filtration.Compounds 39e41 were purified by column chromatographywith petroleum ether/acetone as the eluent. Most of the crudeproducts were crystallized from methanol, except 27 (acetone/petroleumether), 34, 43-48, 50-52 (ethanol) and 42, 49 (toluene). Inthe case of compound 10, the two E/Z isomers were isolated byfractional crystallization from methanol.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Morigi, Rita; Locatelli, Alessandra; Leoni, Alberto; Rambaldi, Mirella; Bortolozzi, Roberta; Mattiuzzo, Elena; Ronca, Roberto; Maccarinelli, Federica; Hamel, Ernest; Bai, Ruoli; Brancale, Andrea; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 166; (2019); p. 514 – 530;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7699-18-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7699-18-5 name is 5-Methoxyindolin-2-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

An oven-dried flask was charged with BBr3.SMe2 (2.80 g, 9.20 mmol) and 1,2-dichloroethane (15 mL). 5-Methoxyindolin-2-one (0.3Og, 1.84 mmol) was then added and the mixture was heated to reflux for 18 hours. The reaction was then cooled to room temperature and quenched with MeOH (1.0 mL). The mixture was then extracted into EtOAc washing with brine (3X). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo; the resulting residue was then purified by column chromatography (silica gel, 94:6 to 92:8, CH2Cl2/Me0H) to give 144 mg, 53 % of a beige powder. MS ESI 149.9 [M + H]+, calcd for [C8H7NO2+ H]+ 150.06

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methoxyindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7699-18-5, name is 5-Methoxyindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7699-18-5, Safety of 5-Methoxyindolin-2-one

General procedure: 4.4.6 (Z)-3-((2-(3-fluorophenyl)-1H-benzo[d]imidazol-6-yl)methylene)-5-methoxyindolin-2-one (5f) Compound 5f was prepared according to the method described for compound 5a, employing aldehyde 11b (120 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 111 mg, 0.83 mmol) to obtain the pure product 5f as a yellow solid (109 mg, 57%); mp: 196-198 C; IR (KBr): 3424, 3167, 2359, 2340, 1697, 1608, 1452, 1414, 1231, 1207, 1020, 840, 746 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.43 (bs, 1H), 8.29-8.22 (m, 2H), 7.99 (s, 1H), 7.79 (s, 1H), 7.76 (d, J = 8.4 Hz, 1H), 7.62 (d, J = 8.3 Hz, 1H), 7.44 (t, J = 8.8 Hz, 2H), 7.32 (d, J = 1.5 Hz, 1H), 6.89-6.72 (m, 2H), 3.62 (s, 3H); 13C NMR (75 MHz, DMSO-d6): delta 168.8, 164.9 and 161.6 (d, J = 248.4 Hz), 153.8, 152.0, 137.4, 136.4, 129.0 (d, J = 8.2 Hz), 128.3, 126.5, 125.9, 124.3, 121.9, 116.0 (d, J = 22.0 Hz), 14.6, 110.2, 108.6, 55.2; MS (ESI): m/z 386 [M + H]+; HRMS (ESI): calcd for C22H17O2N3F m/z 386.12946 [M + H]+; found 386.12993.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Methoxyindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The appropriate oxindole 1 (5 mmol) was dissolved in acetic acid (25 mL) and treated with an equivalent of appropriate indole-3-carbaldehyde 2 and 37% hydrochloric acid (1 mL). The reaction mixture was refluxed for 20 h, the solid separated on cooling was collected by filtration. The crude products were purified by crystallization with ethanol to give the desired products, with the exception of compound 6 purified by column chromatography, with petroleum ether/acetone as the eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methoxyindolin-2-one, its application will become more common.

Reference:
Article; Leoni, Alberto; Locatelli, Alessandra; Morigi, Rita; Rambaldi, Mirella; Cappadone, Concettina; Farruggia, Giovanna; Iotti, Stefano; Merolle, Lucia; Zini, Maddalena; Stefanelli, Claudio; European Journal of Medicinal Chemistry; vol. 79; (2014); p. 382 – 390;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7699-18-5, name is 5-Methoxyindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7699-18-5, name: 5-Methoxyindolin-2-one

General procedure: To a solution of the corresponding substituted oxindole (5, 40 mmol) and triethylamine (88 mmol) in THF (140 mL) was added phenyl chloroformate (13.76 g, 11.0 mL, 88 mmol) dropwise. The temperature was kept below 30 C during the addition. After stirring for 30 min at room temperature, the solvent was evaporated. Water (40 mL) was added to the residue and the mixture was stirred for 2 h at 0-5 C. The crystalline product was filtered and recrystallized from ethyl acetate to give compounds 6.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Porcs-Makkay, Marta; Volk, Balazs; Kokai, Eszter; Simig, Gyula; Tetrahedron; vol. 68; 5; (2012); p. 1427 – 1435;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 7699-18-5 as follows. Recommanded Product: 7699-18-5

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Methoxyindolin-2-one

General procedure: To a one-neck round-bottom flask equipped with magnetic stirringwas added 6-chloro-2-indolinone (2a, 1.00 g, 6.0 mmol),vinamidinium salt 324 (2.02 g, 12.0 mmol), Et3N (1.82 g, 18.0mmol), and DMF (10 mL). The mixture was stirred for 20 h atr.t., after the reaction was complete (monitored by TLC,EtOAc/MeOH = 20:1), 30 mL EtOAc and 30 mL water was added,then the aqueous layer was extracted with 30 mL EtOAc. Thecombined EtOAc layer was washed with sat. NaCl solution (15mL) and water (15 mL) then dried over Na2SO4. After filteringthe desiccant, the solvent was concentrated under vacuum to avolume of about 5 mL. The mixture was titrated with 15 mL nhexaneto give a yellow precipitant, the solid was filtered, anddried under vacuum to give 4a (1.34 g, yield 88%), a yellowpowder, which was used in the next step without further purification;mp > 250 C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Tian, Shaixiao; Mao, Yu; Jiang, Yongjun; Xu, Guangyu; Synlett; vol. 29; 7; (2018); p. 949 – 953;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

7699-18-5, name is 5-Methoxyindolin-2-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C9H9NO2

General procedure: 3-(Propan-2-yliden)indolin-2-one (7a): A solution of indolin-2-one (500 mg, 3.76 mmol, 1.0 equiv.) in acetone (15 mL, 0.25 M) was heated in the presence of catalytic amounts of morpholine (164 mL, 164 mg, 1.88 mmol, 0.5 equiv.) for 16 h at reflux temperature. After complete consumption of the indolin-2-one (determined by thin layer chromatography (TLC)) all volatiles were removed under vacuum. Column chromatography(column diameter 5 cm, 30 g silica, v/v (P/EA)6 : 4-1 : 1) afforded the title compound (650 mg, 3.75 mmol, 99 %) as a yellow solid. Apparent multiplets which occur as a result of accidental equality of coupling constants to those of magnetically non-equivalent protons are marked as virtual (virt.). RF 0.70 (P/EA3 : 7; UV). deltaH (CDCl3, 250 MHz,300 K) 7.96 (1H, br s, NH), 7.52 (1H, br d, 3J 7.7, H-4), 7.19(1H, virt. td, 3JE3J 7.7, 4J 1.2, H-6), 7.01 (1H, virt. td, 3JE3J7.7, 4J 1.2, H-5), 6.85 (1H, ddd, 3J 7.7, 4J 1.2, 5J 0.6, H-7), 2.62(3H, s, H-30), 2.39 (3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K)169.5 (s, C-2), 155.7 (s, C-2′), 139.3 (s, C-7a), 127.7 (d, C-6),124.6 (s, C-3), 123.9 (d, C-5), 123.0 (s, C-3a), 121.8 (d, C-4),109.3 (d, C-7), 25.4 (q, C-1′), 23.3 (q, C-3′). The NMR data match the values reported in the literature.[9] 5-Methoxy-3-(propan-2-ylidene)indolin-2-one (7g): Prepared from 5-methoxy-2-oxindole according to RP 1 on a938 mmol scale. The title compound (176 mg, 866 mmol, 92 %) was obtained as a yellow solid. RF 0.45 (P/EA1 : 1; UV). numax(ATR)/cm1 3150w, 3030w, 2938w, 2836w, 1694vs (CO),1619s, 1594w, 1479s, 1305m, 1203w. deltaH (CDCl3, 250 MHz,300 K) 8.07 (1H, s, NH), 7.14 (1H, d, 4J 1.6, H-4), 6.78-6.72(2H, m, H-6/H-7), 3.81 (3H, s, OCH3), 2.62 (3H, s, H-3′), 2.36(3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K) 169.8 (s, C-2), 156.0(s, C-3′), 155.2 (s, C-5), 133.4 (s, C-7a), 125.6 (s, C-3a), 123.4 (s,C-3), 111.9 (d, C-4), 111.8 (d, C-6), 109.3 (d, C-7), 56.1 (q,OCH3), 25.3 (q, C-1′), 23.3 (q, C-30). m/z (HRMS ESI)204.1019; [M H)](C12H13NO2) requires 204.1019.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maturi, Mark M.; Poethig, Alexander; Bach, Thorsten; Australian Journal of Chemistry; vol. 68; 11; (2015); p. 1682 – 1692;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 5-Methoxyindolin-2-one

B. (E)-3-((3-(4-((dimethylamino)methyl)styryl)-l-((2-(trimethylsilyl)indazol-6-yl)methylene)-5-methoxyindolin-2-one[00108] Piperidine (0.01 mL, 0.1 mmol) was added to a solution of 5-methoxyoxindole (52 mg, 0.32 mmol) and (E)-3-(4-((dimethylamino)methyl)styryl)-l-((2- (trimethylsilyl)ethoxy)-methyl)-lH-indazole-6-carbaldehyde (contaminated with TBAF from previous deprotection attempt, 95.5 mg, 0.22 mmol) in EtOH (5 mL). The reaction was then heated to 75C for 25 hrs. The solvent was evaporated in vacuo. Chromatography (5g silica SPE tube, Silicycle, 5-10% MeOH in CH2C12) gave a brown oil (105 mg, contained product and TBAF by NMR). The residue was dissolved in EtOAc (100 mL) and washed with brine (3 x 15 mL), dried over Na2S04 and the solvent was evaporated in vacuo to give the title compound as a brown oil (1 lOmg, used without further purification).

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 7699-18-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 7699-18-5 as follows.

Preparation of 5-methoxy-2-(1 -methyl-1 H-pyrazol-4-yl)-indole-3-carbaldehyde; 5-Methoxy isatin (0.2 g, 1.1 mmol, 1 eq.) was dissolved in hydrazine hydrate (1.2 ml_, 38 mmol, 34 eq.) and refluxed for 15 minutes. The reaction mixture was poured into cold water and extracted with EtOAc. The combined organic extracts were dried on Na2SO4. The solvent was evaporated to afford crude 5-methoxy-1 ,3-dihydro-indol-2-one that was purified by silica gel column chromatography (eluent: hexane/EtOAc from 10:0 to 6:4). Yield: 27%. MS (m/z): 164.2 (MH+).Phosphorous oxybromide (0.35 ml_, 3.1 mmol, 2.5 eq.) was added drop wise to a solution of DMF (0.3 ml_, 3.7 mmol, 3 eq.) in dry methylene chloride at 00C. The mixture was stirred at 00C for 30 minutes, then a solution of 5-methoxy-1 ,3-dihydro-indol-2-one (0.2 g, 1.2 mmol, 1 eq.) in dry methylene chloride (2 ml_) was added and the mixture was refluxed for 3 hours. The solution was neutralized with solid NaHCO3 and extracted with methylene chloride. The organic layer was dried on Na2SO4 and evaporated under reduced pressure. The crude mixture was purified by silica gel column chromatography (eluent: hexane/AcOEt 6:4 to 4:6) to give pure 2-bromo-5-methoxy-indole-3-carbaldehyde. Yield: 45%. MS (m/z): 254.1 (MH+). A stirred solution of 2-bromo-5-methoxy-indole-3-carbaldehyde (2.0 g, 7.9 mmol, 1 eq.) in DME (2 ml_) was deoxygenated by bubbling argon for 10 minutes at rt. Pd(PPh3)4 (0.9 g, 0.8 mmol, 0.1 eq.) was added followed by a solution of 1-methyl-4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazole (2.4 g, 1 1.63 mmol, 1.48 eq.) in ethanol (2.5 ml_). 2M Na2CO3 (33 ml_, 8.5 eq.) was also deoxygenated with argon and added. The resulting mixture was heated at 78C for 18 hours. The reaction mixture was cooled to room temperature, quenched with water, and extracted with methylene chloride. Organic layer was dried on anhydrous Na2SO4 and evaporated under reduced pressure to give the crude product 1f. Yield: 89%. MS (m/z): 256.1 (MH+).

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH LLC; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; TSOU, Hwei-Ru; ZHANG, Nan; VENKATESAN, Aranapakam M.; DI, Li; KERNS, Edward H.; WO2010/30727; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem