4-Bromo-2-nitroaniline → 4-Bromobenzene-1,2-diamine

HRID 2390402Notes

Reaction equation

HRID 2390402 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[CH:3]=1>C1COCC1.[Pt]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:6])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 701324-Bromo-2-nitroaniline

Product 1

HCID 3235934-Bromobenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-2-nitroaniline (10 g, 46 mmol) in THF (120 mL) was treated with 1% Pt/C (1.0 g) and hydrogenated at room temperature under 40 psi of H2 pressure. After 2 hours, the reaction was filtered and the filtrate concentrated to provide the title compound which was used without further purification in the next step. MS 188 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 6.77-6.81 (m, 2H), 6.54 (d, J=8.4 Hz, 1H), 3.28 (br, 4H).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f1406c0a1c8e424fbc7941f854f08b54
Source dataset
uspto-grants-2012_09
Patent number
US08273767B2

Reaction notes

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