Gamma-Aminobutyric Acid → 4-[(2-Methylacryloyl)amino]butanoic acid
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:8][C:9]([C:11](Cl)=[O:12])=[CH2:10].C(#N)C.Cl>[OH-].[Na+].O.[N+](C1C=CC=CC=1)([O-])=O>[C:11]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])(=[O:12])[C:9]([CH3:10])=[CH2:8]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
In a solution of 38 g of sodium hydroxide, 200 ml of water, and 2 ml of nitrobenzene was dissolved 100 g of γ-aminobutyric acid while stirring, followed by cooling to 0° C. To the aqueous solution were added simultaneously 107.5 g of methacryl chloride and an aqueous solution of 45 g of sodium hydroxide in 100 ml of water. After completion of the reaction, 400 ml of acetonitrile was added thereto. After the reaction mixture was made acidic with 80 ml of concentrated hydrochloric acid, the mixture was extracted with acetonitrile. The resulting acetonitrile extract was concentrated to obtain 149 g of oily N-methacryloyl-γ-aminobutyric acid.
Workup
- additionwas added
- extractionthe mixture was extracted with acetonitrile
- extractionThe resulting acetonitrile extract
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-0e86536023684d4a9eadb17bb295139b
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04746602
Reaction notes
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