Triethyl Phosphate → Ethyl 1-ethyl-7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525949노트

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HRID 525949 반응식
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][NH:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].P(OCC)(OCC)(O[CH2:30][CH3:31])=O>O>[CH2:30]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:12]=2[O:13][CH3:14])[C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9]1)[CH3:31]

참가 물질

5

반응물 3

HCID 6535Triethyl PhosphateHCID 11430Potassium CarbonateHCID 86732817Ethyl 4-hydroxy-7,8-dimethoxyquinoline-3-carboxylate

생성물 1

HCID 15675313Ethyl 1-ethyl-7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate수율 59%

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of ethyl 7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (40 g, 144 mmol) and potassium carbonate (29.9 g, 216 mmol) in triethyl phosphate (123 ml, 721 mmol) was stirred at 120° C. for 24 h. LCMS indicated completion of the reaction. The reaction mixture was cooled down to rt and diluted with water, extracted with DCM, dried over sodium sulfate and evaporated in vacuo. The crude material was recrystallized in EtOH, the precipitate was collected by filtration, washed by cold EtOH and dried in air to afford ethyl 1-ethyl-7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (26 g, 85 mmol, 59.0% yield) as a yellow solid. LCMS: (M+H)+: 306.2.

후처리

  1. customcompletion of the reaction
  2. temperatureThe reaction mixture was cooled down to rt
  3. extractionextracted with DCM
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe crude material was recrystallized in EtOH
  7. filtrationthe precipitate was collected by filtration
  8. washwashed by cold EtOH
  9. customdried in air

출처 및 근거

ORD 기록
ord-7090ebedfdb8456c86d6328edb9893ff
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340556B2

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