Hydrogen Bromide → 7-Hydroxy-3-methyl-2(1H)-quinolinone

HRID 1500546Notes

Reaction equation

HRID 1500546 reaction equation
Br.C[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([CH3:15])[C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1>O>[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([CH3:15])[C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 52904958HCID 52904958, compound

Product 1

HCID 574675147-Hydroxy-3-methyl-2(1H)-quinolinoneYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

47% hydrobromic acid (60 ml) suspension of 2.12 g of 7-methoxy-3-methyl-1H-quinolin-2-one was refluxed for six hours. After cooling, water was added to the reaction solution and precipitated crystals were separated by filtration. The crystals were dissolved in a mixed solvent of dichloromethane and methanol and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure and 1.7 g of 7-hydroxy-3-methyl-1H-quinolin-2-one was obtained in the form of a brown powder.

Workup

  1. temperaturewas refluxed for six hours
  2. temperatureAfter cooling
  3. customprecipitated crystals
  4. customwere separated by filtration
  5. dissolutionThe crystals were dissolved in a mixed solvent of dichloromethane and methanol
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7ed1f0205ac543808fda8f6bf56749b8
Source dataset
uspto-grants-2015_12
Patent number
US09206167B2

Reaction notes

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