Ethanolamine → N-(2-Hydroxyethyl)-4-nitrobenzamide

Participants

Reaction Steps

A solution of 10 ml. ethanolamine in 120 ml. 10% aqueous sodium hydroxide solution was cooled to 5° C. and 30 g. finely powdered 4-nitrobenzoyl chloride added thereto portionwise. The reaction mixture was stirred for 24 hours and filtered. The solid obtained, which mainly consisted of bis-(4-nitrobenzoyl)-ethanolamine, was hydrolysed with 200 ml. of 4% aqueous ethanolic sodium hydroxide at ambient temperature for 24 hours. The reaction mixture was added to the above filtrate, acidified and the precipitated 4-nitrobenzoic acid was filtered off. The filtrate was concentrated and the 13 g. of precipitated N-4-nitrobenzoylethanolamine isolated. The mother liquor was distilled to dryness and the residue was boiled with ethanol. Concentration of the ethanolic extract gave a further 5.3 g. of product; m.p. 134°-135° C.

Provenance & Evidence