(2-Methyl-4-nitrophenyl)(pyridin-2-yl)methanol → (4-Amino-2-methylphenyl)(pyridin-2-yl)methanol

HRID 856600Notes

Reaction equation

HRID 856600 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[OH:12]>C(O)C.[C].[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[OH:12])=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 1

HCID 11447916(2-Methyl-4-nitrophenyl)(pyridin-2-yl)methanol

Product 1

HCID 11390249(4-Amino-2-methylphenyl)(pyridin-2-yl)methanolYield 57.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(2-methyl-4-nitrophenyl)(pyridin-2-yl)methanol (0.83 g) was dissolved in ethanol (50 ml), and the solution was reduced by catalytic hydrogenation overnight with 10% palladium-carbon of 50% hydration (50 mg). The catalyst was removed, and the solvent of the filtrate was distilled off and the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give (4-amino-2-methylphenyl)(pyridin-2-yl)methanol (0.42 g) as colorless crystals.

Workup

  1. customThe catalyst was removed
  2. distillationthe solvent of the filtrate was distilled off
  3. customthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-252ad9f0929049c2acb66c8a599eb8a0
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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