2-Pyridinamine, N-methyl- → ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-[N-methyl-N-(2-pyridyl)aminomethyl]quinoline-3-carboxylate

HRID 266160

反応式

HRID 266160 の反応式
Cl[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N:4]=1.[CH3:32][NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1>COCCO>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([C:11]2[C:10]3[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=3)[N:4]=[C:3]([CH2:2][N:33]([CH3:32])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

参加物

4

反応物 2

HCID 207272-Pyridinamine, N-methyl-HCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

生成物 1

HCID 19032340ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-[N-methyl-N-(2-pyridyl)aminomethyl]quinoline-3-carboxylate収率 9%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

実験手順

A mixture of ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (1.0 g), 2-(methylamino)pyridine (0.95 g) and 2-methoxyethanol (30 ml) was stirred under reflux for 17 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with hexane - ethyl acetate (3:2, v/v) gave ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-[N-methyl-N-(2-pyridyl)aminomethyl]quinoline-3-carboxylate (0.1 g, 9%). This compound was recrystallized from dichloromethane-ethanol. Pale yellow prisms, mp. 174°-175° C.

後処理

  1. temperatureunder reflux for 17 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe fractions eluted with hexane - ethyl acetate (3:2

出典と根拠

ORDレコード
ord-c6b16c641ff143efbe0a37014a7cb0db
出典データセット
uspto-grants-1997_07
特許番号
US05650410

関連ノート

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