(2-Bromo-3-methoxy-6-nitro-phenyl)-phenylamine → 3-Bromo-4-methoxy-N2-phenylbenzene-1,2-diamine

HRID 243075Notes

Reaction equation

HRID 243075 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-])=O)[C:3]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOC(C)=O.[Pd]>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([NH2:10])[C:3]=1[NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 68157845(2-Bromo-3-methoxy-6-nitro-phenyl)-phenylamine

Product 1

HCID 681572213-Bromo-4-methoxy-N2-phenylbenzene-1,2-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-bromo-3-methoxy-6-nitro-phenyl)-phenylamine (470 mg, 1.81 mmol) in EtOAc (15 mL) was added palladium on carbon (100 mg, 10% by wt) and the reaction mixture stirred at RT under an atmosphere of hydrogen for 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo to give the title compound as a yellow solid (426 mg, 100%). 1H NMR 400 MHz δ (CDCl3): 7.24-7.17 (2H, m), 6.89-6.83 (1H, m), 6.74-6.72 (1H, m), 6.68-6.63 (2H, m), 5.48 (1H, br s), 3.85 (3H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f2bd984c9c31437b922ddb5d20862a11
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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