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

A sodium hydroxide solution (3.35 g in 25 ml of water, 0.084 moles) is added dropwise to a solution of 12 g methyl 4-dimethylaminocrotonate (0.084 moles) in 100 ml methyl alcohol at room temperature. The reaction mixture is heated to 40–45° C. for 1 hour then cooled to room temperature. The pH is adjusted to about 1˜2 with 5 N HCl. The mixture was concentrated to a thick oil, which is triturated with dehydrated alcohol to form a solid. The solid by-product is filtered and the filtrate is evaporated to an oil, which is triturated with isopropyl alcohol to afford 7.0 g of white solid product. Yield is 50% with the purity 86.3% by GC-MS.

1. temperatureThe reaction mixture is heated to 40–45° C. for 1 hour
2. concentrationThe mixture was concentrated to a thick oil, which
3. customis triturated with dehydrated alcohol
4. customto form a solid
5. filtrationThe solid by-product is filtered
6. customthe filtrate is evaporated to an oil, which
7. customis triturated with isopropyl alcohol

ORD record

ord-437012e123834b238eafca93b2e56438

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07126025B2