Sulfuric Acid → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetic acid ethyl ester

HRID 266124

反応式

HRID 266124 の反応式
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=O.[CH3:29][CH2:30][O:31][C:32]([CH2:34][C:35]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=O)=[O:33]>C(O)(=O)C>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([C:9]2[C:8]3[C:7](=[CH:24][C:23]([O:25][CH3:26])=[C:22]([O:27][CH3:28])[CH:21]=3)[N:6]=[C:35]([CH2:34][C:32]([O:31][CH2:30][CH3:29])=[O:33])[C:37]=2[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 66045Diethyl acetonedicarboxylateHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

生成物 1

HCID 117990276,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetic acid ethyl ester収率 64.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

Conc. sulfuric acid (1.5 ml) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (50.0 g), diethyl acetonedicarboxylate (35.0 g) and acetic acid (400 ml), and the mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was poured into water, neutralized with an aqueous saturated solution of sodium bicarbonate, and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residual crystals were recrystallized from acetone to give ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3-ethoxycarbonylquinoline-2-acetate (48.8 g, 64%). Colorless prisms, mp. 146°-147° C.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was poured into water
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residual crystals were recrystallized from acetone

出典と根拠

ORDレコード
ord-ef881ca9d2034a3ba0e5b9106fd38325
出典データセット
uspto-grants-1997_07
特許番号
US05650410

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