HCID 22938867, compound → HCID 22938900, compound

HRID 856604Notes

Reaction equation

HRID 856604 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[CH:12]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1)[OH:13]>C(OCC)(=O)C.C(O)C.[C].[Pd]>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([CH:12]([C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=2)[OH:13])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 1

HCID 22938867HCID 22938867, compound

Product 1

HCID 22938900HCID 22938900, compoundYield 33.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-methoxy-4-nitrophenyl)(4-methylpyridin-2-yl)methanol (2.2 g) was dissolved in ethyl acetate (50 ml) and ethanol (50 ml), and the solution was reduced by catalytic hydrogenation overnight with 10% palladium-carbon of 50% hydration (150 mg). The catalyst was removed, and the solvent of the filtrate was distilled off. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give (4-amino-2-methoxyphenyl)(4-methylpyridin-2-yl)methanol (0.65 g) as pale yellow 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-d5594421fe494236800631873a4542d5
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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