HCID 67021331, compound → HCID 67021591, compound

HRID 1660973Notes

Reaction equation

HRID 1660973 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[N+:20]([O-])=O)=[CH:8][CH:7]=1)[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[NH2:20])=[CH:10][CH:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67021331HCID 67021331, compound

Product 1

HCID 67021591HCID 67021591, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of [4-(4-bromo-2-nitro-phenylamino)-phenyl]-acetic acid ethyl ester (1.0 g, 2.64 mmol) and Raney Ni (˜0.300 g) in EtOH (20 mL) is stirred for 2.5 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of Celite and concentrated. Silica gel column chromatography purification (Hexane/EtOAc, 7:3) of the crude product affords the title compound as a pale pink solid: ES-MS: 351.0 [M+2]+; single peak at tR=4.82 min (System 1); Rf=0.16 (Hexane/EtOAc, 7:3).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of Celite
  2. concentrationconcentrated
  3. customSilica gel column chromatography purification (Hexane/EtOAc, 7:3) of the crude product

Sources & evidence

ORD record
ord-d5bb02499761437390f36662b1a0fe7b
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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