Beta-Alanine → 3-[(2-Nitrophenyl)amino]propanoic acid

HRID 1709224Notes

Reaction equation

HRID 1709224 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].C(N(CC)CC)C.O>CN(C)C=O>[C:14]([CH2:13][CH2:12][NH:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 962WaterHCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 30902033-[(2-Nitrophenyl)amino]propanoic acidYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5.0 g (36 mmol) 2-fluoronitrobenzen, 6.3 g (71 mmol) β-alanin, 20 ml triethylamine, 50 ml water and 100 ml dimethylformamide was stirred at 80° C. for 10 h. After cooling to 25° C. the reaction mixture was evaporated in vacuo. The residue was stirred with IN hydrochloric acid, and the precipitate was filtered off and washed with water to give 3.6 g (48%) N- carboxyethyl-2-nitroaniline. M.p. 145° C., 1H-NMR (DMSO-d6): 8.2-6.2 (5H, m), 3.4 (2H, q), 2.5 (2H, t).

Workup

  1. temperatureAfter cooling to 25° C. the reaction mixture
  2. customwas evaporated in vacuo
  3. stirringThe residue was stirred with IN hydrochloric acid
  4. filtrationthe precipitate was filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-147e6b1023dd4679ba3504529a8aac60
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Reaction notes

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