Beta-Alanine → 3-{[2-Nitro-4-(trifluoromethyl)phenyl]amino}propanoic acid

HRID 1458870Notes

Reaction equation

HRID 1458870 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium Carbonate

Product 1

HCID 27643443-{[2-Nitro-4-(trifluoromethyl)phenyl]amino}propanoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

60 g (0.27 mol) of 2-chloro-1-nitro-5-trifluoromethylbenzene, 50 g (0.56 mol) of β-alanine and 41 g (0.3 mol) of potassium carbonate were refluxed in a mixture of 300 ml of dimethylformamide and 50 ml of water for 6 h. The mixture was then poured into ice-water, the aqueous phase was acidified with hydrochloric acid, and the precipitate was filtered off with suction to yield 73 g (99%) of the product.

Workup

  1. filtrationthe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-0d450953e7f74e069213f9f7a9a10ee7
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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