Triethylamine → 5-Bromo-2-methoxyaniline

HRID 1060342Notes

Reaction equation

HRID 1060342 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.C(N(CC)CC)C>[Ni].C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:3]=1)[NH2:10]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 1185334-Bromo-2-nitroanisole

Product 1

HCID 35853285-Bromo-2-methoxyanilineYield 104.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-bromo-2-nitro-anisole (7.7 g, 33.1 mmol), triethylamine (4.6 ml, 33.1 mmol) and Raney Nickel catalyst (4 g) was vigorously stirred in ethanol (300 ml) under an atmosphere of hydrogen for 1 h at 20° C. After this time the theoretical amount of hydrogen had been absorbed (2.5 1), so the catalyst was filtered off and the solvent evaporated to afford the title compound as a light yellow solid (7 g, 104% yield), MS: m/e=201 (M+).

Workup

  1. customAfter this time the theoretical amount of hydrogen had been absorbed (2.5 1)
  2. filtrationso the catalyst was filtered off
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-202940cd8c8348048c7d15ccb8b147a5
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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