Phosphorus oxychloride → Ethyl 2-chloro-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate

HRID 1458947ノート

反応式

HRID 1458947 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=O)[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]2[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1.P(Cl)(Cl)([Cl:33])=O>>[Cl:33][C:8]1[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 22097611ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2(1H)-quinolone-3-carboxylate

生成物 1

HCID 21801288Ethyl 2-chloro-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate収率 73%

反応条件

温度
105 °C

実験手順

A mixture of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2(1H)-quinolone-3-carboxylate (5.0 g) and phosphorus oxychloride (POCl3)(6.3 ml) was stirred at 100 to 110° C. for 80 minutes. The reaction mixture was concentrated under reduced pressure. The residue was poured into water, neutralized with an aqueous saturated sodium bicarbonate solution and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with chloroform gave ethyl 2-chloro-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (3.8 g, 73%) which was then recrystallized from ethyl acetate-hexane. mp. 168°-169° 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
  7. washThe fractions eluted with chloroform

出典と根拠

ORDレコード
ord-f9aebf00a61b4bd0bda451aa8b7d6ff0
出典データセット
uspto-grants-1998_12
特許番号
US05852039

反応ノート

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