Gamma-Aminobutyric Acid → 4-p-Anisamidobutyric acid

HRID 1164307Notes

Reaction equation

HRID 1164307 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].[OH-].[Na+].Cl>O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 1557234-p-Anisamidobutyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.2 g. of p-methoxybenzoyl chloride are added at 30° C. in one portion while stirring well to 30.9 g. of 4-amino-butyric acid, 24.0 g. of sodium hydroxide and 300 ml. of ion-free water. After 2 hours, the mixture is acidified with 75 ml. of concentrated hydrochloric acid at a temperature below 10° C. The precipitate is filtered off, washed ion-free with water, dried in a drying oven at 65° C. over phosphorus pentoxide and then recrystallized from 45 ml. of acetone/low-boiling petroleum ether (3:1). There is obtained 4-(p-methoxybenzoylamino)butyric acid having a melting point of 120.5°-122° C.

Workup

  1. customat a temperature below 10° C
  2. filtrationThe precipitate is filtered off
  3. washwashed ion-free with water
  4. dry with materialdried in a drying oven at 65° C. over phosphorus pentoxide
  5. customrecrystallized from 45 ml

Sources & evidence

ORD record
ord-3d0f711387b542e7a617fc3bced348da
Source dataset
uspto-grants-1983_01
Patent number
US04369139

Reaction notes

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