Реакция #1076558

Уравнение реакции

4-chloro-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile

3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine

pyridine hydrochloride

→

4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile

Выход 65.6%

Растворители

2-ethoxyethanol

sodium carbonate

Условия реакции

Обработка

1. 1
   Температураcooled to room temperature
2. 2
   Фильтрацияthe solid is collected by filtration
3. 3
   ПромывкаThe solid is washed with water
4. 4
   Другоеdried in vacuo
5. 5
   ДругоеThe crude product is purified by silica gel chromatography

Методика

A mixture of 1.0 g (3.53 mmol) of 4-chloro-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, 0.93 g (3.88 mmol) of 3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine and 0.41 g (3.52 mmol) of pyridine hydrochloride in 20 mL of 2-ethoxyethanol is heated at 120° C. for 2 hours, then cooled to room temperature. The product mixture is diluted with a saturated solution of sodium carbonate, stirred for 15 minutes and the solid is collected by filtration. The solid is washed with water and dried in vacuo. The crude product is purified by silica gel chromatography, utilizing a 95:5 to 9:1 gradient of methylene chloride/methanol to give 1.13 g of 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid, mp>300° C.

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