HCID 66650288, compound → 2-(4-hydroxy-phenyl)-1h-quinolin-4-one

HRID 418854Notes

Reaction equation

HRID 418854 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=1)=O>Br>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[NH:1][C:2]3[C:3]([C:8](=[O:20])[CH:9]=2)=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 66650288HCID 66650288, compound

Product 1

HCID 116300562-(4-hydroxy-phenyl)-1h-quinolin-4-oneYield 99%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1-(2-Amino-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione (375 mg, 1.49 mmol) was dissolved in 48% HBr (15 mL) and refluxed for 16 h. The solvent was removed at reduced pressure. The solids were taken into water and neutralized by NaHCO3. Solids were collected and purified by column chromatography using 5% MeOH in DCM to give 350 mg of 2-(4-hydroxy-phenyl)-1H-quinolin-4-one (98%). MS (ES): m/z: 238.1 (M+1).

Workup

  1. temperaturerefluxed for 16 h
  2. customThe solvent was removed at reduced pressure
  3. customSolids were collected
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-4f22793304594abea55b879b93e29cfa
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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