Hydrochloric Acid → (2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride

Participants

Reaction Steps

A solution of sodium hydroxide (6.2 g, 0.155 mol, 4 equiv) in water (40 ml) was added to a stirred solution of (E)-methyl 4-(dimethylamino)but-2-enoate hydrochloride (7 g, 0.039 mol, 1.00 equiv) in methanol (150 ml). The reaction mixture was stirred for 4 hours. 6N hydrochloric acid was added to bring the pH to 2. The reaction mixture was concentrated under reduced pressure, and ethanol (50 ml) was added and the solid was removed by filtration. The filtrate was concentrated under reduced pressure to thick oil. The oil was crystallized in isopropanol and acetone to give the product 3.6 g. MS (ESI) m/z: 563 (M+1).

Provenance & Evidence