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

HRID 525949ノート

反応式

HRID 525949 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7090ebedfdb8456c86d6328edb9893ff
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

反応ノート

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