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

HRID 1418981Notes

Reaction equation

HRID 1418981 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-10e375cb391145279a84fea2032ff194
Source dataset
uspto-grants-1999_03
Patent number
US05885996

Reaction notes

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