(4-Methoxycarbonylphenyl)-(3-hydroxypyridin-4-yl)-methanol hydrochloride → 4-(4-Methoxycarbonylbenzyl)-3-hydroxypyridine

HRID 2116490Notes

Reaction equation

HRID 2116490 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[OH:20])O)=[CH:8][CH:7]=1)=[O:5]>[Pd].CO>[CH3:2][O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[OH:20])=[CH:10][CH:11]=1)=[O:5]

Participants

4

Reactant 1

HCID 23103650(4-Methoxycarbonylphenyl)-(3-hydroxypyridin-4-yl)-methanol hydrochloride

Product 1

HCID 231036354-(4-Methoxycarbonylbenzyl)-3-hydroxypyridineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Next, a mixture of (4-methoxycarbonylphenyl)-(3-hydroxypyridin-4-yl)-methanol hydrochloride (1.87 g, 5.50 mmol), methanol (50 ml) and 10% palladium/carbon (0.94 g) was stirred under a hydrogen atmosphere at room temperature for 3 days. After filtration to remove the insoluble materials, the filtrate was concentrated under reduced pressure and the resulting residue was poured into saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting crystal was recrystallized from diethyl ether to give the titled compound (1.27 g, 95%).

Workup

  1. filtrationAfter filtration
  2. customto remove the insoluble materials
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionthe resulting residue was poured into saturated aqueous NaHCO3
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crystal was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-2b7bf570d3154c73af2b6f98d5817ece
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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