4-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one → 3,3-Dimethylquinoline-2,4(1H,3H)-dione

HRID 1097777Notes

Reaction equation

HRID 1097777 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]1([CH3:14])[CH3:13]>CN(C=O)C.C(Cl)Cl.O=[Mn]=O>[CH3:13][C:3]1([CH3:14])[C:2](=[O:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12]

Participants

4

Reactant 1

HCID 592777124-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 138366743,3-Dimethylquinoline-2,4(1H,3H)-dioneYield 69%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A mixture of 4-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one (1.0 g, 5.2 mmol) and MnO2 (4.5 g, 52 mmol) in DMF-CH2Cl2 (10%, v/v, 20 mL) is heat to reflux for overnight (˜16 h). The insoluble material is removed by filtration through a pad of celite (˜1 cm), and washed with CH2Cl2. The combined solution is concentrated under vacuum, and yields the title compound as colorless solid (675 mg, yield 69%).

Workup

  1. temperatureis heat
  2. temperatureto reflux for overnight (˜16 h)
  3. customThe insoluble material is removed by filtration through a pad of celite (˜1 cm)
  4. washwashed with CH2Cl2
  5. concentrationThe combined solution is concentrated under vacuum

Sources & evidence

ORD record
ord-d58b983c11f3487c8ac9ff64f19ffadd
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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