Tag: M.W=100-200

480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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: Method A: To a stirred suspension of the appropriate nitrogen derivative II (0.16 mmol) and chlorophosphine gold(l) compound III (0.16 mmol) in MeOH (2 mL) was added dropwise NaOMe (0.5 M in MeOH , 0.18 mmol). The reaction was stirred at rt for 16 h before concentrating in vacuo to give a solid residue which was suspended in DCM (2 mL) and filtered. The filtrate was concentrated in vacuo giving an oily residue which after trituration with Et.20 (x 3) and drying under high vacuum for 16 h, provided the title compound I. Method E: As Method A except the reaction mixture was heated at 50 C for 18 h.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AUSPHERIX LIMITED; HOLMES, Ian; NAYLOR, Alan; ALBER, Dagmar; POWELL, Jonathan Raymond; MAJOR, Meriel Ruth; NEGOITA-GIRAS, Gabriel; ALLEN, Daniel Rees; GUETZOYAN, Lucie Juliette; KING, Nigel Paul; CHAPMAN, Nicholas Andrew; (155 pag.)WO2017/93545; (2017); A1;,
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 100487-74-9 as follows. 100487-74-9

Preparation 29 6-Chloro-5-fluoro-indole To a solution of 6-chloro-5-fluoro-oxindole (0.49 g, 2.64 mmol) in THF (5 mL) was added slowly 1M BH3 in THF (21.2 mL, 21.2 mmol) over 30 minutes. The mixture was stirred 24 hours and 1N aqueous NaOH (25 mL) was added carefully with stirring. After stirring 20 minutes the mixture was extracted with EtOAc/Et2 O (1:1), and the extracts were combined, washed with brine, dried over Na2 SO4(s), filtered and concentrated in vacuo to afford 412 mg of the product as a mixture of 6-chloro-5-fluoroindole and 6-chloro-5-fluoroindoline (GC-MS: 169, and 171 (M+), respectively),which was used without further purification.

According to the analysis of related databases, 100487-74-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1914-02-9, A common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, 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.

Example 37 1. Synthesis of intermediate 037-2 The intermediate 001-5 (2.22 g, 14.9 mmol), anhydrous THF (25 mL), 037-1 (1.5 g, 10.2 mmol) and DIPEA (2.58 g, 20.0 mmol) were added into a 100 mL single-necked flask sequentially, and then the reaction was heated to 75C and maintained under stirring for 2.5 h. The reaction was cooled to room temperature, and the reaction mixture was subjected to rotary evaporation, and the crude product was purified through silica gel column chromatography (eluent: EA:PE = 1:15) to give 1.5 g of the intermediate 037-2 (57%) as a white solid. LCMS: 260.1.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Shaletech Technology Co., Ltd.; JIANG, Yueheng; (143 pag.)EP3216786; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2913-97-5, name is N-(2-Oxoethyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows., 2913-97-5

Step 2: A mixture of aniline 107 (1 37 g, 6 7 mmol), 2-(l,3-dioxoisoindohn-2-yl)acetaldehyde (108)(1 26 g, 6 7 mmol), sodium tnacetoxyborohydnde (2 1 g, 10 05 mmol), and acetic acid (0 04 g, 6 7 mmol) in dry dichloromethane under argon was stirred at room temperature for 2 h The reaction mixture was washed with saturated aqueous NaHCO3, water, and brine The combmed organics were dried over Na2SO4 filtered, and concentrated under reduced vacuum Flash chromatography (0-60percent EtOAc – hexanes gradient), gave the secondary aniline 109 as a yellow oil Yield (1 6 g, 64percent) 1H NMR (400 MHz, CDCl3) delta 7 80 – 7 85 (m, 2H), 7 66 – 6 72 (m, 2H), 7 01 (t, J = 6 Hz, IH)1 6 18 – 6 22 (m, 2H), 6 14 – 6 18 (m, IH), 4 05 (br s, IH), 3 95 (t, J= 6 0 Hz, 2H), 3 68 (d, /= 6 4 Hz, 2H), 3 41 (t, J= 6 4 Hz, 2H), 1 80 – 1 88 (m, 2H), 1 64 – 1 78 (m, 4H), 1 12 – 1 34 (m, 3H), 0 96 – 1 08 (m, 2H)

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:
Patent; ACUCELA INC.; WO2009/45479; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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. 2913-97-5

General method for the synthesis of compound 7: Phthalimidoacetaldehyde 4 (0.378 g, 2 mmol) was dissolved in 6 mL of acetonitrile. To this solution added 6-bromoindole 5a (0.780 g, 2 mmol), barbituric acid 6 (0.312 g, 2 mmol), and catalytic amount of D-L-Proline under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 24 h. The resulting suspension was filtered and the precipitate was washed with acetonitrile (2 .x. 50 mL) to obtain a white compound 7a. The product 7a was obtained in a 95percent yield (1.00 g), m.p 107-108 ¡ãC. 1H NMR (300 MHz, CDCl3): delta 2.84 (s, 3H), 3.05 (s, 3H), 3.86 (d, 1H), 4.33 (m,1H), 4.70 (d, 2H), 7.05-8.01 (m, 8H), 8.23 (br s, 1H). Similarly compound 7b-c were synthesised and characterised.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2913-97-5.

Reference:
Article; Seetham Naidu; Bhuyan, Pulak J.; Tetrahedron Letters; vol. 53; 4; (2012); p. 426 – 428;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3484-35-3 name is 5-Methylindolin-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. 3484-35-3

General procedure: Equimolar quantity of 5-substituted-1H-indolin-2-ones and 2-(4-formylphenoxy)-N-substituted-phenyl-acetamide was taken into round bottom flask containing 50 mL of methanol, followed by 2-3 drops of piperidine. The reaction mixture was refluxed for 1-4 h or till the end of reaction as confirmed by TLC. Then, it was cooled to room temperature and, the solution was filtered. The obtained residue was recrystallized by using dimethylformamide and ethanol.

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

Reference:
Article; Bhadauria, Vivek Singh; Sravanthi, Vishnu; Kumar, Sujeet; Das, Debajyoti; De Clercq, Erik; Schols, Dominique; Tokuda, Harukuni; Karki, Subhas S.; Acta poloniae pharmaceutica; vol. 74; 1; (2017); p. 137 – 145;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2913-97-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of S-I-Il (6.26 g) and TEA (10.04 g) in dichloromethane (100 mL) at 5-10 ¡ãC was added hydroxylamine hydrochloride (2.53 g). The mixture was stirred at room temperature for 15 h and then quenched with NH4C1(aq) (50 mL, 2M). The aqueous phase was extracted with CH2C12 (2×50 mL). The combined organic NaHCO3(aq)sulfate, filtered. The filtrate was concentrated to get the crude product S-I-Ill (4.01 g, y: 59percent).

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATIONAL HEALTH RESEARCH INSTITUTES; SHIH, Chuan; SHIA, Kak-Shan; WU, Chien-Huang; CHOI, Ming-Chen; SONG, Jen-Shin; WANG, Yun; (84 pag.)WO2018/132326; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

61-70-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 61-70-1, name is 1-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Preparation of 1-methyl-5-nitro-1,3-dihydro-indol-2-one 1-Methyl-1,3-dihydro-indol-2-one (Step 1, 2.10 g, 14.3 mmol) is added in portions to 70% nitric acid (10 ml) at -10 C. After the addition is complete, the reaction is allowed to warm to room temperature and then stirred for 5 hours. The mixture is diluted with ice water and the resulting precipitate filtered, washed with water, and dried under vacuum to give the title compound as a brown solid. HPLC r.t. 3.97 min; MS for C9H8N2O3 m/z 193.9(M+H)+.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luehr, Gary W.; Jain, Rama; Renslo, Adam; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail F.; US2006/30609; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, A common compound: 317-20-4, name is 7-Fluoroisatin, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A mixture of 5-chloroisatin (1.81 mg,10 mmol), 1-bromobutane (2 mL, 18 mmol) and cesium carbonate (13.03 g, 40 mmol) in dimethylformamide (100 mL) was stirred at room temperature overnight. After extraction with ethyl acetate, the organic layer was washed with hydrochloric acid (0.4 N) and water, dried over MgSO4 and concentrated under vacuum, giving a residue that was washed with a mixture of heptane-ethyl acetate to afford 1-butyl-5-chloroindoline-2,3-dione (2a, 2.13 g, 90%) as a red solid. The same procedure was used to prepare 2b-d.

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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Reddy, Sanapalli Subba; Pallela, Ramjee; Kim, Dong-Min; Won, Mi-Sook; Shim, Yoon-Bo; Chemical and Pharmaceutical Bulletin; vol. 61; 11; (2013); p. 1105 – 1113;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, 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. 774-47-0

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 774-47-0.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem