HCID 11594031, compound → 2-(5-Hydroxy-pyridin-2-yl)-chromen-4-one

HRID 884705Notes

Reaction equation

HRID 884705 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[O:19])[CH:18]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:7][CH:8]=1>I.CC(O)=O.O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[O:19])[CH:18]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:7][CH:8]=1

Participants

5

Reactant 1

HCID 11594031HCID 11594031, compound

Product 1

HCID 116731392-(5-Hydroxy-pyridin-2-yl)-chromen-4-oneYield 36.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 24841Hydrogen iodideSolvent

Procedure

2-(5-Methoxy-pyridin-2-yl)-chromen-4-one (790 mg, 3.12 mmol) in HI (10 mL) and AcOH (4 mL) was heated at reflux for 6 h. Reaction mixture was cooled to rt, diluted with water, neutralized and extracted with EtOAc to give crude product. This was purified by column chromatography using 5% MeOH in dichloromethane to give (270 mg, 36%) of 2-(5-Hydroxy-pyridin-2-yl)-chromen-4-one. MS (ES) m/z: 240.09 (M+1).

Workup

  1. temperatureat reflux for 6 h
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. customto give crude product
  5. customThis was purified by column chromatography

Sources & evidence

ORD record
ord-216a17a503f24780aa4c399a64494fd6
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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