2,3-Difluoro-4-methyl-6-nitrophenol → 6-Amino-2,3-difluoro-4-methyl-phenol

HRID 2060003Notes

Reaction equation

HRID 2060003 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[CH:5]=[C:4]([N+:10]([O-])=O)[C:3]=1[OH:13].[H][H]>C(O)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[CH:5]=[C:4]([NH2:10])[C:3]=1[OH:13]

Participants

5

Reactant 2

HCID 594441602,3-Difluoro-4-methyl-6-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 594441706-Amino-2,3-difluoro-4-methyl-phenolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2,3-difluoro-4-methyl-6-nitrophenol (1.2 g, 6.35 mmol) (D44) in ethanol (120 mL) was hydrogenated using a 10% Pd/C cartridge in the H-cube™ hydrogenator at 1 mL/min and full hydrogen at 25° C. Evaporation gave 2,3-difluoro-4-methyl-6-aminophenol (1.0 g, 6.28 mmol, 99% yield) as a fawn solid.

Workup

  1. customat 25° C
  2. customEvaporation

Sources & evidence

ORD record
ord-a22a99d8e4da4ec3a1964e8613f35293
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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