Gamma-Aminobutyric Acid → HCID 135674608, compound

HRID 280278Notes

Reaction equation

HRID 280278 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].C[O-].[Na+].[Cl:11][C:12]1[CH:13]=[C:14]([CH3:28])[C:15]([OH:27])=[C:16]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=O)[CH:17]=1.C(O)C>CO>[Cl:11][C:12]1[CH:13]=[C:14]([CH3:28])[C:15]([OH:27])=[C:16]([C:18](=[N:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 702EthanolHCID 30211374',5-Dichloro-2-hydroxy-3-methylbenzophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 135674608HCID 135674608, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Aminobutanoic acid (2.2 g; 0.0213 mol), sodium methoxide (1.16 g; 0.0213 mol) and (5-chloro-2-hydroxy-3-methylphenyl)-(4-chlorophenyl)-methanone (6 g; 0.0213 mol) are introduced into a mixture of 200 ml of ethanol and 400 ml of methanol, and the resulting mixture is then evaporated to dryness. Ethanol (500 ml) is added to the residue and the mixture is then evaporated to dryness. The latter operation is repeated 4 times. The residue is dissolved in 1 liter of water and the pH is acidified to pH 4 by the addition of citric acid. The precipitate is filtered off, washed with water and then dissolved in CH2Cl2. The organic solution is washed with water, dried (MgSO4) and filtered, and the filtrate is evaporated to give an oil, which is crystallised once from petroleum ether and recrystallised twice from AcOEt.

Workup

  1. customthe resulting mixture is then evaporated to dryness
  2. additionEthanol (500 ml) is added to the residue
  3. customthe mixture is then evaporated to dryness
  4. dissolutionThe residue is dissolved in 1 liter of water
  5. additionthe pH is acidified to pH 4 by the addition of citric acid
  6. filtrationThe precipitate is filtered off
  7. washwashed with water
  8. dissolutiondissolved in CH2Cl2
  9. washThe organic solution is washed with water
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe filtrate is evaporated
  13. customto give an oil, which
  14. customis crystallised once from petroleum ether
  15. customrecrystallised twice from AcOEt

Sources & evidence

ORD record
ord-dc723d912eb64682bf767dbedf9e0b22
Source dataset
uspto-grants-1986_05
Patent number
US04588748

Reaction notes

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