ethyl 6-(N,N-diethylamino)-3-oxohexanoate → ethyl 2-[3-(N,N-diethylamino)propyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 266149ノート

反応式

HRID 266149 の反応式
Cl.[NH2:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=O.[CH2:25]([N:27]([CH2:30][CH2:31][CH2:32][C:33](=O)[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:28][CH3:29])[CH3:26]>C(O)C>[CH2:25]([N:27]([CH2:30][CH2:31][CH2:32][C:33]1[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=2)[C:4]2[C:3](=[CH:20][C:19]([O:21][CH3:22])=[C:18]([O:23][CH3:24])[CH:17]=2)[N:2]=1)[CH2:28][CH3:29])[CH3:26]

参加物

4

反応物 2

HCID 19032338ethyl 6-(N,N-diethylamino)-3-oxohexanoateHCID 214661342-Amino-3',4',4,5-tetramethoxybenzophenone hydrochloride

生成物 1

HCID 19032363ethyl 2-[3-(N,N-diethylamino)propyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate収率 14%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone hydrochloride (7.7 g), ethyl 6-(N,N-diethylamino)-3-oxohexanoate (5.0 g) and ethanol (100 ml) was stirred under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform. The chloroform layer was washed with an aqueous saturated solution of sodium bicarbonate and water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-methanol (20:1, v/v) gave ethyl 2-[3-(N,N-diethylamino)propyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (1.51 g, 14%). This compound was recrystallized from ethanol-hexane. Colorless prisms, mp. 96°-98° C.

後処理

  1. temperatureunder reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe chloroform layer was washed with an aqueous saturated solution of sodium bicarbonate and water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. washThe fractions eluted with chloroform-methanol (20:1

出典と根拠

ORDレコード
ord-b2f55d19a0fb4d078104a328740f906a
出典データセット
uspto-grants-1997_07
特許番号
US05650410

反応ノート

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