2-Fluoro-4-methyl-6-nitrophenol → 2-Amino-6-fluoro-4-methylphenol

HRID 1798930Notes

Reaction equation

HRID 1798930 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[OH:12].[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[OH:12]

Participants

5

Reactant 2

HCID 227538152-Fluoro-4-methyl-6-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 552821212-Amino-6-fluoro-4-methylphenolYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-fluoro-4-methyl-6-nitrophenol (400 mg, 2.337 mmol) (D15) in ethanol (50 mL) was hydrogenated using a Pd/C cartridge in the H-cube™ hydrogenator at 1 mL/min and full hydrogen. Evaporation gave 2-fluoro-4-methyl-6-aminophenol (250 mg, 1.771 mmol, 76% yield) as a fawn solid.

Workup

  1. customEvaporation

Sources & evidence

ORD record
ord-567bc3c7879a4419b18a4d83be338342
Source dataset
uspto-grants-2013_01
Patent number
US08344000B2

Reaction notes

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