Sodium Hydroxide → N-(2-Methyl-1,2,3,4-tetrahydroisoquinolin-8-yl)-4-acetylamino-5-chloro-2-methoxybenzamide

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Reaction Steps

To a cooled solution of 4-acetylamino-5-chloro-2-methoxybenzoyl chloride, (prepared from 4-acetylamino-5-chloro-2-methoxybenzoic acid, 3.19 g) in dichloromethane was added 8-amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (2.1 g) and triethylamine (4 ml). After stirring at room temperature for 2.5h, the mixture was basified with 10% sodium hydroxide. The organic layer was separated, dried and concentrated in vacuo. The residue was purified by chromatography on alumina eluting with chloroform, and then crystallised from ethyl acethate to give the title compound.

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