Acetone → 8-Methoxy-6-nitro-3,4-dihydroquinolin-2(1H)-one

HRID 1649001Notes

Reaction equation

HRID 1649001 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([OH:14])[CH:13]=1)[NH:10][C:9](=[O:15])[CH2:8][CH2:7]2)([O-:3])=[O:2].[C:16](=O)([O-])[O-].[K+].[K+].CC(C)=O.S(OC)(OC)(=O)=O>O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:14][CH3:16])[CH:13]=1)[NH:10][C:9](=[O:15])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 130510728-Hydroxy-6-nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 130510718-Methoxy-6-nitro-3,4-dihydroquinolin-2(1H)-oneYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Nitro-8-hydroxy-3,4-dihydrocarbostyril (10 g) and potassium carbonate (13.3 g) were mixed with acetone (70 ml) and water (70 ml) and the mixture was refluxed with adding dropwise 12.1 g of dimethyl sulfate. After refluxing was continued for 4 hours, the reaction mixture was cooled, and crystals which precipitated were collected by filtration and washed with water to give 8.22 g of 6-nitro-8-methoxy-3,4-dihydrocarbostyril.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter refluxing
  3. temperaturethe reaction mixture was cooled
  4. customcrystals which precipitated
  5. filtrationwere collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-ce801d41c2ee4dc780258c800ebf7e7a
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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