5-Bromo-N-ethyl-2-nitroaniline → 5-broMo-N1-ethylbenzene-1,2-diaMine

HRID 2370381Notes

Reaction equation

HRID 2370381 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([NH:8][CH2:9][CH3:10])[CH:7]=1>[Ni].CO.C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([NH2:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 249029765-Bromo-N-ethyl-2-nitroaniline

Product 1

HCID 592936595-broMo-N1-ethylbenzene-1,2-diaMineYield 85.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A suspension of (5-bromo-2-nitro-phenyl)-ethyl-amine (Step 26.3) (6 g, 24.48 mmol) and Raney nickel (2 g) in MeOH/THF (1:1 v/v, 600 mL) is stirred for 9 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated. The residue purified by silica gel column chromatography (Hex/EtOAc, 95:5→85:15) to afford 4.51 g of the title compound as a black oil: ESI-MS: 213.1/215.1 [M−H]−; tR=2.53 min (System 1); TLC: Rf=0.57 (Hex/EtOAc, 1:1).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe residue purified by silica gel column chromatography (Hex/EtOAc, 95:5→85:15)

Sources & evidence

ORD record
ord-7b7c68b1a6b24f4594e248526ce1c355
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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