Furo[3,2-c]pyridine → 2H,3H-furo(3,2-c)pyridine

HRID 2389867

Reaction equation

HRID 2389867 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1>C(O)(=O)C.[C].[Pd]>[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 12234604Furo[3,2-c]pyridine

Product 1

HCID 155348962H,3H-furo(3,2-c)pyridineYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of furo[3,2-c]pyridine (500 mg, 4.20 mmol) in acetic acid (8 mL) was added 5% palladium-carbon powder (manufactured by WAKO, 250 mg), and the mixture was stirred at room temperature for 24 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (365 mg, yield 72%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. additionsaturated aqueous sodium hydrogen carbonate solution was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c355e5d3ad8e43d9a38ccb52049025b8
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Linked notes

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