HCID 136341208, compound → 2-Amino-4-fluoro-6-methylphenol

HRID 1460569Notes

Reaction equation

HRID 1460569 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]([OH:9])[C:4](C2C=CC=CC=2)([N:10]=NC2C=CC=CC=2O)[CH:3]=1>C(OCC)(=O)C.[Pd]>[NH2:10][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([CH3:8])[C:5]=1[OH:9]

Participants

4

Reactant 1

HCID 136341208HCID 136341208, compound

Product 1

HCID 156759522-Amino-4-fluoro-6-methylphenolYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.75 g (25 mmoles) of 4-fluoro-6-methyl-2-phenylazophenol (B1) and 1.1 g of 5% Pd/c in ethyl acetate was shaken in a Parr shaker under hydrogen at room temperature for 17.5 hours. The reaction mixture was filtered through celite and the filtrate concentrated to an oil which was purified on silica gel eluting with hexane-ethyl acetate, giving 3.2 g of a white solid: m.p. 97° C. (dec).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate concentrated to an oil which
  3. customwas purified on silica gel eluting with hexane-ethyl acetate

Sources & evidence

ORD record
ord-7705d81af164466f81711407ae904e9e
Source dataset
uspto-grants-1991_12
Patent number
US05071863

Reaction notes

Loading…