HCID 178436444, compound → HCID 178436189, compound

HRID 2116503Notes

Reaction equation

HRID 2116503 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[OH:15])=O)=[CH:5][CH:4]=1)[CH3:2]>[OH-].[OH-].[Pd+2].CO>[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[OH:15])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 178436444HCID 178436444, compound

Product 1

HCID 178436189HCID 178436189, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst3×HCID 887MethanolSolvent

Procedure

Next, a mixture of 3-(4-ethylbenzoyl)-4-hydroxypyridine (2.69 g, 0.0118 mol), 20% palladium hydroxide/carbon (530 mg) and methanol (60 mL) was stirred under a hydrogen atmosphere for 18 hours. Additional 20% palladium hydroxide/carbon (300 mg) was added and stirred for 6 hours, followed by further addition of 20% palladium hydroxide/carbon (340 mg) and stirring for 15 hours. After filtration to remove the insoluble materials, the filtrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give 3-(4-ethylbenzyl)-4-hydroxypyridine (2.09 g, 83%) as a colorless amorphous substance.

Workup

  1. stirringstirred for 6 hours
  2. stirringstirring for 15 hours
  3. filtrationAfter filtration
  4. customto remove the insoluble materials
  5. customthe filtrate was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-97231aaffe714603a02fa8883528ca1c
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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