Hydrochloric Acid → Ethyl 3-(3-chloroanilino)propanoate

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Reaction Steps

3-Chloroaniline (3.8 g, 0.03 moles) was dissolved in ethanol (5 ml) and ethyl acrylate (3.3 g, 0.033 moles) was added in ethanol (5 ml). Concentrated hydrochloric acid (1 ml) was added and the reaction mixture was heated at reflux for 48 hours. Evaporated to a low bulk and dissolved the residue in dichloromethane and water. Basified to pH 9 with aqueous ammonia and separated. Evaporated off the dichloromethane under reduced pressure to give the crude product as a yellow oil (5.4 g) Purified using a silica column eluted with isohexane:ethyl acetate 9:1 to give the required product (3.5 g, 51%) as a colourless oil.

Provenance & Evidence