(3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester → Ethyl 2-(2-amino-3-bromophenylamino)acetate

HRID 1056028Notes

Reaction equation

HRID 1056028 reaction equation
[Br:1][C:2]1[C:3]([N+:15]([O-])=O)=[C:4]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1>O.CCO.C1COCC1.[Ni]>[NH2:15][C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 1

HCID 59392671(3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester

Product 1

HCID 59392693Ethyl 2-(2-amino-3-bromophenylamino)acetate

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Raney 2800 nickel, in water (Aldrich; 8 mL) was added to a solution of ethyl 2-((3-bromo-2-nitrophenyl)amino)acetate (14.12 g, 46.6 mmol) in EtOH (290 ml) and THF (290 ml); the mixture was placed under an atmosphere of H2 and was stirred at RT for 20 h. The mixture was filtered through a pad of wet Celite, topped with sand, and washed with DCM to give ethyl 2-((2-amino-3-bromophenyl)amino)acetate (210c) as a brown liquid. MS (ESI, pos. ion) m/z: 273.0/275.0 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of wet Celite
  2. washwashed with DCM

Sources & evidence

ORD record
ord-c1d37e37886249e8940b5659bc6cd6a5
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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