4-Fluoro-2-methyl-5-nitrophenol → 5-Amino-4-fluoro-2-methylphenol

HRID 450440Notes

Reaction equation

HRID 450440 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([OH:11])=[C:4]([CH3:12])[CH:3]=1>CO.[Pd]>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([CH3:12])=[C:5]([OH:11])[CH:6]=1

Participants

4

Reactant 1

HCID 108210594-Fluoro-2-methyl-5-nitrophenol

Product 1

HCID 101540985-Amino-4-fluoro-2-methylphenolYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-fluoro-2-methyl-5-nitro-phenol (1.4 g, 8.2 mmol) and 10% Pd/C (0.3 g, 20%/w) in MeOH (80 mL) was stirred under H2 (30 psi) for 2 h. The Pd/C was removed by filtration and the filtrate was concentrated to give 5-amino-4-fluoro-2-methyl-phenol (0.68 g, 62% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.75 (s, 1H), 6.62 (d, J=12.0 Hz, 1H), 6.21 (d, J=8.1 Hz, 1H), 4.69 (s, 2H), 1.93 (s, 3H).

Workup

  1. customThe Pd/C was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1dbf7a552cab41daa142941fea9d8466
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

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