2-Bromo-1-ethyl-4-nitrobenzene → 3-Bromo-4-ethylaniline

HRID 1665772Notes

Reaction equation

HRID 1665772 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][CH3:12]>CO.[Ni]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH2:11][CH3:12])[NH2:8]

Participants

4

Reactant 1

HCID 223455942-Bromo-1-ethyl-4-nitrobenzene

Product 1

HCID 223456173-Bromo-4-ethylanilineYield 210.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-1-ethyl-4-nitro-benzene (25 g, 0.019 mol) in MeOH (100 mL) was added Raney-Ni (2.5 g). The reaction mixture was hydrogenated under hydrogen (1 atm) at room temperature. After stirring for 3 hours, the mixture was filtered and concentrated under reduced pressure. The crude material was purified by preparative HPLC to give 3-bromo-4-ethylaniline (8.0 g, 48%). 1H NMR (400 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1 H), 6.83 (d, J=2.4 Hz, 1 H), 6.52 (dd, J=2.4, 8.4 Hz, 1 H), 2.57 (q, J=7.6 Hz, 2 H), 1.10 (t, J=7.6 Hz, 3 H). MS (ESI) m/e (M+H+) 200.

Workup

  1. customwas hydrogenated under hydrogen (1 atm) at room temperature
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-151a7a7def034e28a49e59b6726838ea
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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