2-Bromo-4-nitrotoluene → Benzenamine, 3-bromo-4-methyl-

HRID 725809Notes

Reaction equation

HRID 725809 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH3:11]>CO.[Ni]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH3:11])[NH2:8]

Participants

4

Reactant 1

HCID 821892-Bromo-4-nitrotoluene

Product 1

HCID 82187Benzenamine, 3-bromo-4-methyl-Yield 95.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 50.0 g (0.23 mol) 2-Bromo-4-nitro-toluene in 500 ml methanol was placed in a Parr hydrogenation bottle. To the solution was added 5.0 g Raney nickel. This mixture was hydrogenated at 30 psi H2 on the Parr hydrogenator for three hours with agitation. The Parr bottle was vented, the reaction mixture was filtered through diatomaceous earth (celite), and the filtrate was evaporated to yield 41.0 g (95%) of a yellow oil. IR (neat) 3329, 3144, 2604, 1609, 1288, 1030, 812 cm-1 ; 1H NMR (DMSO-d6) δ 2.13 (s, 3H), 5.60 (bs, 2H), 6.46 (dd, 1H, J=8.1 Hz, 2.3 Hz), 6.79 (d, 1H, J=2.3 Hz), 6.94 (d, 1H, J=8.2 Hz). HRMS calcd. for C7H8BrN: 184.9843. Found: 184.9840.

Workup

  1. filtrationthe reaction mixture was filtered through diatomaceous earth (celite)
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0c4d610fc4c2469aa1e9b32baff0362c
Source dataset
uspto-grants-1998_01
Patent number
US05707992

Reaction notes

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