Gamma-Aminobutyric Acid → 4-[(2-Methylacryloyl)amino]butanoic acid

HRID 1263068Notes

Reaction equation

HRID 1263068 reaction equation
[OH-].[Na+].[N+](C1C=CC=CC=1)([O-])=O.[NH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].[C:19](Cl)(=[O:23])[C:20]([CH3:22])=[CH2:21].Cl>O.C(#N)C>[C:19]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:23])[C:20]([CH3:22])=[CH2:21]

Participants

8

Reactant 5

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 7416NitrobenzeneHCID 13528Methacryloyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 187981514-[(2-Methylacryloyl)amino]butanoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

In a mixture composed of 80 g (2.0 mol) of sodium hydroxide, 400 ml of water and 4 ml of nitrobenzene was dissolved with stirring 214 g (2.0 mol) of γ-aminobutyric acid and the mixture was cooled to 0° C. To the aqueous solution, there were simultaneously added dropwise 230 g (2.2 mol) of methacrylic chloride and an aqueous solution containing 96 g (2.4 mol) of sodium hydroxide dissolved in 200 ml of water. After the completion of the reaction, 800 ml of acetonitrile was added to the reaction solution and the mixture was then acidified by adding 160 ml of concentrated hydrochloric acid and extracted with acetonitrile. The acetonitrile solution was concentrated to obtain 318.4 g of N-methacryloyl-γ-aminobutyric acid as an oily product.

Workup

  1. dissolutionwas dissolved
  2. additionwas added to the reaction solution
  3. extractionextracted with acetonitrile
  4. concentrationThe acetonitrile solution was concentrated

Sources & evidence

ORD record
ord-370cde1bc85a44a093b45bbfa810b2bf
Source dataset
uspto-grants-1984_06
Patent number
US04455366

Reaction notes

Loading…