Diethyl Carbonate → HCID 20375644, compound

HRID 1833377Notes

Reaction equation

HRID 1833377 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.[H-].[Na+].[C:21](=[O:28])([O:25][CH2:26][CH3:27])OCC>O>[O:18]=[C:4]1[CH:3]=[C:2]([CH:1]([C:21]([O:25][CH2:26][CH3:27])=[O:28])[C:21]([O:25][CH2:26][CH3:27])=[O:28])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 2691834-methyl-1-phenylquinolin-2(1h)-one

Product 1

HCID 20375644HCID 20375644, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,2-dihydro-4-methyl-2-oxo-1-phenylquinoline (4.7 g.), sodium hydride (4.8 g., 60% w/w dispersion in oil, washed as in Example 1) and diethyl carbonate (50 ml.) was stirred under reflux for 2 hours. Any excess of sodium hydride was then destroyed by addition of methanol to the cooled suspension, and the mixture was then poured into ether (1 l.). The yellow precipitate was collected by filtration, and washed with ether (200 ml.). It was suspended in ethanol (50 ml.), concentrated hydrochloric acid was added to give a pH of 3, and the resultant solution was poured into water (200 ml.). The precipitate was extracted into ether, and the combined extracts were washed with water, dried over magnesium sulphate, and evaporated in vacuo. A sample of the residual solid was recrystallised from a mixture of benzene and cyclohexane to give diethyl 1,2-dihydro-2-oxo-1-phenylquinol-4-ylmalonate, m.p. 101°-103° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customAny excess of sodium hydride was then destroyed by addition of methanol to the cooled suspension
  3. additionthe mixture was then poured into ether (1 l.)
  4. filtrationThe yellow precipitate was collected by filtration
  5. washwashed with ether (200 ml.)
  6. additionconcentrated hydrochloric acid was added
  7. customto give a pH of 3
  8. extractionThe precipitate was extracted into ether
  9. washthe combined extracts were washed with water
  10. dry with materialdried over magnesium sulphate
  11. customevaporated in vacuo
  12. customA sample of the residual solid was recrystallised from a mixture of benzene and cyclohexane

Sources & evidence

ORD record
ord-e5983052c0b649359588aaceab63d5b5
Source dataset
uspto-grants-1978_01
Patent number
US04066651

Reaction notes

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