Ammonium Chloride → 3,5-Diaminobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester

Participants

Reaction Steps

1.0 g (1.99 mmol) of 3,5-dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester and 0.42 g (7.96 mmol) of ammonium chloride were suspended in 20 ml of a mixture consisting of methanol : water 9:1. 2.6 g (39.8 mmol) of zinc were then added in portions in the course of 30 minutes. After 2 hours at room temperature 20 ml of methanol were added. After a further 17 hours the reaction suspension was partitioned between methylene chloride and water and the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water. The organic phase was then dried over magnesium sulphate, filtered and concentrated by evaporation. Chromatography of the residue on 150 g of silica gel using ethyl acetate yielded 0.84 g of 3,5-diaminobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester.

Provenance & Evidence