Triethylamine → Methyl 4-(3-hydroxyanilino)-4-oxobutanoate

Participants

Reaction Steps

To an ice cold solution of 3-aminophenol (21.8 g, 0.2 mol) and triethylamine (21.3 g, 0.2 mol) in tetrahydrofuran (250 ml) is added a solution of 3-carbomethoxypropanoyl chloride (30.1 g, 0.2 mol) in tetrahydrofuran. The reaction is allowed to warm to room temperature and is filtered through a pad of Celite and silica gel. The solvent is removed in vacuo to give a solid. Recrystallization from ethyl acetate gives 39.3 g (88% yield) of product, m.p. 144.5°-146° C.

Provenance & Evidence