5-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 7-(Benzyloxy)-6-methoxyquinolin-4-ol

HRID 393596ノート

反応式

HRID 393596 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[NH:12][CH:13]=[C:14]1[C:19](=[O:20])OC(C)(C)OC1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:24]([C:19](=[O:20])[CH:14]=[CH:13][NH:12]2)=[CH:25][C:26]=1[O:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 226465295-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

生成物 1

HCID 226465797-(Benzyloxy)-6-methoxyquinolin-4-ol収率 82%

試薬・触媒・溶媒 1

HCID 7583Diphenyl Ether溶媒

反応条件

温度
45 °C

実験手順

5-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (10 g, 26 mmol) was rapidly added to phenyl ether (150 ml) heated at reflux. The mixture maintained a vigorous reflux for 5 minutes, and was allowed to cool to 45° C. then poured into petroleum ether. The resulting solid was collected by filtration and purified by column chromatography eluting with methylene chloride/methanol (95/5 followed by 90/10 and 85/5) to give 7-benzyloxy-6-methoxy-1,4-dihydroquinolin-4-one (6 g, 82%) as a yellow solid.

後処理

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe mixture maintained
  4. temperaturea vigorous reflux for 5 minutes
  5. filtrationThe resulting solid was collected by filtration
  6. custompurified by column chromatography
  7. washeluting with methylene chloride/methanol (95/5 followed by 90/10 and 85/5)

出典と根拠

ORDレコード
ord-5f77c3214b3e48d6abebb94eb417fe66
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

反応ノート

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