Water → Methyl 3-(3-amino-4-chlorophenyl)propanoate

Participants

Reaction Steps

Under reflux, 0.86 ml (11.7 mmol) of thionyl chloride was added dropwise to a solution of 1.0 g (3.91 mmol) of tert-butyl 3-(3-amino-4-chlorophenyl)propanoate in 20 ml of methanol. The mixture was stirred under reflux for 1.5 h and then, after cooling, diluted with dichloromethane. The solution was added to water, and after phase separation the organic phase was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The residue was dried under high vacuum. This gave 745 mg (90.3% of theory) of the target compound.

Provenance & Evidence