4-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester → 3-Amino-4-(2-bromopyridin-4-ylamino)benzoic acid methyl ester

HRID 453063Notes

Reaction equation

HRID 453063 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=2)=[C:6]([N+:18]([O-])=O)[CH:5]=1>CO.[Ni]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=2)=[C:6]([NH2:18])[CH:5]=1

Participants

4

Reactant 1

HCID 866585844-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester

Product 1

HCID 866585853-Amino-4-(2-bromopyridin-4-ylamino)benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester 3 (6 g; 17 mmol) was dissolved in MeOH (200 ml) and Raney-nickel (0.6 g; 4.5 mmol) was added and subsequently hydrogenated under an atmosphere of H2 for 3 h. LCMS showed full conversion and the reaction mixture was filtered through a bed of Celite to remove the catalyst. Thorough washing with MeOH followed by evaporation of the solvent under educed pressure gave 4 as a brown solid. Yield 3.2 g; 60%. The product identity was confirmed by NMR and LCMS and taken for the next step.

Workup

  1. filtrationthe reaction mixture was filtered through a bed of Celite
  2. customto remove the catalyst
  3. customThorough washing with MeOH followed by evaporation of the solvent under educed pressure

Sources & evidence

ORD record
ord-afdac5e9bb9049439f626eedc3d52869
Source dataset
uspto-grants-2013_07
Patent number
US08492408B2

Reaction notes

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