Category: 14389-06-1

Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

Reference Example 23 Synthesis of 2-phenyl-6-chloro-8-methylquinoline-4-carboxylic Acid The above-mentioned compound (1.03 g) was formed from 1.95 g of 5-chloro-7-methylisatin and 2.40 g of acetophenone in the same manner as in Reference Example 1. 1 H-NMR(DMSO-d6), delta: 2.53(s, 3H), 7.55(m, 3H), 7.65(d, 1H), 8.03(d, 1H), 8.25(d, 2H), 8.35(s, 1H), 8.46(s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-7-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; Mitsui Toatsu Chemicals, Inc.; US5627193; (1997); A;,
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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. 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Chloro-7-methylindoline-2,3-dione

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 14389-06-1.

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,
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These common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-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. Application In Synthesis of 5-Chloro-7-methylindoline-2,3-dione

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

The synthetic route of 5-Chloro-7-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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Synthetic Route of 14389-06-1, A common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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: To a mixture of 5-chloroisatin (182 mg, 1.0 mmol) and N-carboxyethylrhodanine (205 mg, 1.0 mmol) was added DMSO-d6 (3.0 mL). The reaction was followed by proton NMR until the disappearance of the starting material.

The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xue, Fengtian; MacKerell Jr., Alexander D.; Heinzl, Geoffrey; Hom, Kellie; Tetrahedron Letters; vol. 54; 13; (2013); p. 1700 – 1703;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

[0521] The 5-CHLORO-7-METHYL-LH-INDOLE-2, 3-dione (25.0 g, 0.13 mol), potassium hydroxide (8.4 g, 0.15 mmol) and 30% hydrogen peroxide (21.6 g, 0.18 mol) were mixed together in methanol (300 mL) at 0C for 2 h followed by 16 h at room temperature. The solution was poured into ethyl acetate (500 mL) and extracted with 1 N hydrochloric acid (3 x 200 mL) followed by brine (1 x 50 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The 2-amino-5-chloro-3-methylbenzoic acid (18.0 g, 0.10 mmol) was isolated as a yellow solid (75% yield). HRMS 7NEZ 185.0238 ; calcd 185.0244.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-7-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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Indoline | C8H9N – PubChem

Application of 14389-06-1, The chemical industry reduces the impact on the environment during synthesis 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

To a suspension of 3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (97.6% purity, 13.02 g, 42 mmol) and 5-chloro-7-methylindoline-2,3-dione (K. Tsuji et al., Bioorg. Med. Chem. Letters, 2002, 72(17), pp 2427-2430) (7.82 g, 40 mmol) in dry acetonitrile (50 mL) was added 3-picoline (11.9 g, 127 mmol). The mixture was cooled to 0 C, and then methanesulfonyl chloride (6.87 g, 60 mmol) was added dropwise at 0-10 0C. After stirring 5 minutes at this temperature, the mixture was warmed to room temperature for 20 hours. The precipitated solids were filtered, washed with acetonitrile (3 x 5 mL), and dried under nitrogen to afford the title product, a compound of the present invention, as a yellow powder, 14.90 g (77.6% yield), m.p. 173-177 0C (decomp.).1H NMR (CDCl3) delta 2.16 (s, 3H), 7.14 (s, IH), 7.38 (dd, J = 8.1, 4.8 Hz, IH), 7.53 (d, /= 2.1 Hz, IH), 7.60 (d, /= 2.1 Hz, IH), 7.89 (dd, /= 8.1, 1.5 Hz, IH), 8.39 (dd, / = 4.8, 1.5 Hz, IH). The NMR spectrum also showed that some 3-picoline salts were present in the crude product.

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-Chloro-7-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/24833; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

To a suspension of 3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (97.6% purity, 3.25 g, 10.5 mmol) and 5-chloro-7-methylindoline-2,3-dione (K. Tsuji et al., Bioorg. Med. Chem. Letters, 2002, 12(17), pp 2427-2430) (1.96 g, 10.0 mmol) in dry acetonitrile (12 mL) was added 3-picoline (2.60 g, 28 mmol). The mixture was cooled to 0 C, and then methanesulfonyl chloride (1.48 g, 12.9 mmol) was added dropwise at 0-10 C. After stirring 5 minutes at this temperature, the mixture was warmed to room temperature for 2 hours. Then additional quantities of 3-picoline (0.37 g, 4.0 mmol) and methanesulfonyl chloride (0.24 g, 2.1 mmol) were added, and stirring was continued at room temperature for 3 hours. The mixture was cooled to 0 C, water (6 mL) was added dropwise, and stirring at 0-5 0C was continued for 1 hour. Then the mixture was filtered, and the solids were washed with 2:1 acetonitrile-water (3 x 3 mL), and dried under nitrogen to afford the 3-picoline salt of the title compound as a light green solid, 1.23 g. EPO The isolated solid was suspended in acetonitrile (3 mL) and IN aqueous hydrochloric acid (3 mL) was added dropwise. The solids dissolved, and then a new precipitate formed. The mixture was stirred at room temperature for 1 hour, and the precipitate was filtered, washed with 1 : 1 acetonitrile-water (3 x 2 mL), and dried under nitrogen to afford the title product, a compound of the present invention, as an off-white solid, 0.27 g (5.6% yield), m.p. 139-142 0C.1H NMR (DMSO-^6) delta 2.22 (s, 3H), 7.29 (s, IH), 7.58 (d, J = 2.4 Hz, IH), 7.61 (dd, J = 8.2, 4.6 Hz, IH), 7.71 (d, J = 2.4 Hz, IH), 8.17 (dd, / = 8.2, 1.4 Hz, IH), 8.49 (dd, J = 4.6, 1.4 Hz, IH), 10.57 (br s, IH).

The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/24833; (2007); A1;,
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. 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H6ClNO2

C. 5-Chloro-7-methyl-1 H-indole5-Chloro-7-methyl-1 H-indole-2,3-dione (1.8g, 9.23mmol) is added neat to a 1.0 M solution of lithium aluminum hydride in ether (92mL). The reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched with ice and is diluted with ethyl acetate (60OmL). The organic phase is collected, washed with sat NH4CI (2 XI OOmL) and brine (50 mL). The organic is dried over magnesium sulfate, filtered and concentrated in vacuo to give the crude product. Purification by flashchromatography on SiO2 eluting with 5% ethyl acetate/ heptane gives 1.27 g, (83% yield) of desired product. 1H-NMR (CDCI3, 300 MHz): delta 8.1 (bs, H), 7.45 (s, 1 H), 7.2 (d, 1 H), 7.0 (s, 1 H), 6.5 (d, H), 2.5 (s, 3H). LCMS m/z: [M+H]+=166

The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; CHOI-SLEDESKI, Yong-Mi; GARDNER, Charles, J.; LIANG, Guyan; POLI, Gregory, B.; SHUM, Patrick, Wai-Kwok; STOKLOSA, Gregory, T.; ZHAO, Zhicheng; WO2011/22449; (2011); A1;,
Indoline – Wikipedia,
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