Phosphorus oxychloride → 4-Chlorofuro[3,2-c]pyridine

HRID 2389865Notes

Reaction equation

HRID 2389865 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][NH:6][C:5](=O)[C:4]=2[CH:3]=[CH:2]1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:5]1[C:4]2[CH:3]=[CH:2][O:1][C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2887464H,5H-furo(3,2-c)pyridin-4-one

Product 1

HCID 27797464-Chlorofuro[3,2-c]pyridineYield 81%

Conditions

Temperature
120 °C

Procedure

Furo[3,2-c]pyridin-4(5H)-one (72.2 g, 534 mmol) was added to phosphorus oxychloride (100 mL) heated to 120° C., and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure. Ice-cooled water was added to the residue, and the mixture was basified with 8M aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70) to give the title compound (66.1 g, yield 81%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. temperatureIce-cooled water
  3. additionwas added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70)

Sources & evidence

ORD record
ord-f2672242778245b5a9b9844a63c6f6a7
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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