Diethyl Carbonate → HCID 20375644, 화합물

HRID 1833377노트

반응식

HRID 1833377 반응식
[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

참가 물질

5

반응물 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 2691834-Methyl-1-phenyl-2(1H)-quinolone

생성물 1

HCID 20375644HCID 20375644, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5983052c0b649359588aaceab63d5b5
출처 데이터셋
uspto-grants-1978_01
특허 번호
US04066651

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