2-Bromo-5-(methylamino)-4-nitrobenzonitrile → 4-Amino-2-bromo-5-(methylamino)benzonitrile

HRID 1048994Notes

Reaction equation

HRID 1048994 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH:13][CH3:14])=[CH:6][C:3]=1[C:4]#[N:5]>CCO.[Pd]>[NH2:10][C:8]1[C:7]([NH:13][CH3:14])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Br:1])[CH:9]=1

Participants

4

Reactant 1

HCID 666848622-Bromo-5-(methylamino)-4-nitrobenzonitrile

Product 1

HCID 666852384-Amino-2-bromo-5-(methylamino)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of 2-bromo-5-(methylamino)-4-nitrobenzonitrile (0.3 g, 0.001 mol) in EtOH (10 ml) was hydrogenated using Pd/C for 2 h at room temperature. The reaction was filtered through CELITE® and the filter bed was thoroughly washed with EtOH. The resulting solution was concentrated to provide 4-amino-2-bromo-5-(methylamino)benzonitrile, as a brownish a solid. Crude LCMS (M+1): 226.12. Purity: 63%.

Workup

  1. customfor 2 h
  2. customat room temperature
  3. filtrationThe reaction was filtered through CELITE®
  4. washthe filter bed was thoroughly washed with EtOH
  5. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-938ccd653baa4deda04ebb787abd7c87
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

Loading…