(3-Fluoro-2-methoxy-6-nitrophenyl)phenylamine → 4-Fluoro-3-methoxy-N2-phenylbenzene-1,2-diamine

HRID 243238Notes

Reaction equation

HRID 243238 reaction equation
[F:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([N+:8]([O-])=O)=[CH:6][CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68157646(3-Fluoro-2-methoxy-6-nitrophenyl)phenylamine

Product 1

HCID 681576944-Fluoro-3-methoxy-N2-phenylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-fluoro-2-methoxy-6-nitrophenyl)phenylamine (322 mg, 1.2 mmol) in EtOAc (5 mL) was added palladium on carbon (30 mg, 10% by wt) and the reaction mixture stirred at RT under an atmosphere of hydrogen for 4 hours. The reaction mixture was filtered and the filtrate concentrated in vacuo to give the title compound as a white solid which darkened to red on standing (284 mg, 100%). 1H NMR 400 MHz δ (CDCl3): 7.24-7.18 (2H, m), 6.88-6.78 (2H, m), 6.71-6.66 (2H, m), 6.43 (1H, dd, J=9.0, 4.5 Hz), 5.50 (1H, br s), 3.77 (3H, d, J=1.7 Hz), 3.64 (2H, br s).

Workup

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

Sources & evidence

ORD record
ord-d7fcf85eccdd4b24994dffe3c7dc20dc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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