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

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).

1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethanol (50 ml)
2. additionwas added
3. customthe solid was removed by filtration
4. concentrationThe filtrate was concentrated under reduced pressure to thick oil
5. customThe oil was crystallized in isopropanol

ORD record

ord-4d4692e8e7f04fdd9694057dc05fe7c9

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748453B2