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

HRID 2242742Notes

Reaction equation

HRID 2242742 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, 1H), 6.83 (d, J=2.4 Hz, 1H), 6.52 (dd, J=2.4, 8.4 Hz, 1H), 2.57 (q, J=7.6 Hz, 2H), 1.10 (t, J=7.6 Hz, 3H). 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-a22dfe945d2246fea5f8c275d946d4b4
Source dataset
uspto-grants-2010_03
Patent number
US07671221B2

Reaction notes

Loading…