1-Aminocyclopropane-1-carboxylic acid → Ethyl 1-aminocyclopropane-1-carboxylate hydrochloride

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-aminocyclopropanecarboxylic acid (5.8 g, 57.4 mmol) in 300 mL of ethanol was cooled to 0° C., thionyl chloride (20.5 g, 172.7 mmol) was added drop-wise over 30 minutes. Then the cold bath was removed and the reaction mixture was heated at reflux for 2 hours, then the mixture was stirred at room temperature for 16 hours. The solvent was evaporated at 40° C. under reduced pressure to give ethyl 1-aminocyclopropanecarboxylate hydrochloride (9.53 g, 100%) as a solid. It was used directly in the next step without further purification. MS: (M+H)+=130.2; 1H NMR (300 MHz, DMSO): δ 9.04 (brs, 3H), 4.14 (q, 2H, J=6.9 Hz), 1.45 (d, 2H, J=3.3 Hz), 1.37 (d, 2H, J=3.2 Hz), 1.19 (t, 3H, J=6.9 Hz).

Provenance & Evidence