ChemicalBook CAS DataBase List 6-CHLORO-7-METHYL ISATIN

6-CHLORO-7-METHYL ISATIN synthesis

5synthesis methods

Product Name:6-CHLORO-7-METHYL ISATIN
CAS Number:6374-90-9
Molecular formula:C9H6ClNO2
Molecular Weight:195.6

Ethanimidoyl chloride, N-(3-chloro-2-methylphenyl)-2-(hydroxyimino)-

867154-50-5
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6374-90-9
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Yield:6374-90-9 62%

Reaction Conditions:

with sulfuric acid at 50 - 80; for 0.666667 h;

Steps:

A

To well stirred sulphuric acid (18.3 M, 300 ml) heated at 50°C was added N-(3-chloro-2- methyl-phenyl) -2-hydroxyimino-acetimidoyl chloride (1) in small portion over 20 minutes (exothermic up to 70°C) (60 g, 282 mmol). After addition was completed, the temperature was risen to 80°C and kept for 20 minutes after which the reaction was left cool to room temperature. The brown mixture was slowly poured into ice (-500 g) and water (500 mL), diluted with more water (1 L) to yield a brown-orange slurry. The solid was collected by filtration, washed with water (2X) under suction to yield an orange solid. This solid was dissolved in 0.4 M sodium hydroxide (1 L). All insoluble tar was removed by filtration. Concentrated hydrochloric acid (12 M, 70 mL) was added, the resulting brown-orange solid was collected by filtration, washed with water (3X), heptane (2X) and dried at 54°C under vacuum for 6 hours. Obtained 34.5 g (208 mmol, 62%) of 6-chloro-7-methyl-1H-indole-2,3- dione (2). No.H (400 MHz, DMSO-d6) 11.3 (1 H, s), 7.4 (1 H, d, J=8.0), 7.2 (1 H, d, J=8.1), 2.25 (3 H, s).

References:

WO2005/97107,2005,A2 Location in patent:Page/Page column 35-36

302-17-0 Synthesis