HCID 54695711, compound → Furo[3,2-c]pyridin-3(2H)-one

HRID 1984291Notes

Reaction equation

HRID 1984291 reaction equation
[OH:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1C(OCC)=O>Cl>[O:4]1[C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:2](=[O:1])[CH2:3]1

Participants

3

Reactant 1

HCID 54695711HCID 54695711, compound

Product 1

HCID 14199081Furo[3,2-c]pyridin-3(2H)-oneYield 15.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl 3-hydroxyfuro[3,2-c]pyridine-2-carboxylate (5.79 g, 27.9 mmol) was dissolved in 10% hydrochloric acid (50 mL), and heated under reflux for 40 h. The reaction mixture was evaporated to dryness. The residue was suspended in saturated sodium bicarbonate solution and extracted with chloroform 3 times. The chloroform extracts were combined, dried (MgSO4), filtered, and evaporated to give furo[3,2-c]pyridin-3(2H)-one (570 mg) as a light-brown oil. N,N-Diisopropylethylamine (616 mg, 4.77 mmol) was added slowly to a solution of furo[3,2-c]pyridin-3(2H)-one (560 mg, 4.14 mmol) in dry methylene chloride (25 mL) under nitrogen at −10° C. Then trifluoromethanesulfonic anhydride (1.40 g, 4.97 mmol) was added slowly. The mixture was allowed to warm to RT, and stirred for another 1 g. The reaction was quenched with water. The organic layer was washed with water, dried (MgSO4), filtered, and then the solvent was evaporated to give the sub-title compound as a brown oily residue (1.10 g), which was used without further purification for the next step.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 40 h
  3. customThe reaction mixture was evaporated to dryness
  4. extractionextracted with chloroform 3 times
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b94f9a55e53b4a789ee44185f2992ecf
Source dataset
uspto-grants-2009_06
Patent number
US07544693B2

Reaction notes

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