Ethanol → 2-(4-Cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid

HRID 1086823ノート

反応式

HRID 1086823 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[CH2:13]1[CH2:18][CH2:17][CH:16]([CH:19]([CH3:28])[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24]C=2)=O)[CH2:15][CH2:14]1.[OH-:29].[K+].[CH2:31](O)C>O>[CH:16]1([C:19]2[CH:20]=[CH:22][C:27]([C:26]3[C:25]([CH3:24])=[C:5]([C:6]([OH:11])=[O:29])[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[N:7]=3)=[CH:31][CH:28]=2)[CH2:15][CH2:14][CH2:13][CH2:18][CH2:17]1

参加物

6

反応物 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 2365665-FluoroisatinHCID 67928556HCID 67928556、化合物

生成物 1

HCID 51671812-(4-Cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-Fluoroisatin (100 g, 0.61 mole) and 4-cyclohexylpropiophenone (131 g, 0.61 mole) were suspended in 1100 ml of ethanol and stirred mechanically as a solution of 219 g (5.5 mole) of KOH in 550 ml of water was added dropwise. After the addition was complete, the mixture was heated at reflux for 12 hours, cooled, and the ethanol evaporated under reduced pressure. The resulting solid was dissolved in water and washed with ethyl ether. The aqueous layer was acidified with HCl. The resulting precipitate was filtered and dried. Recrystallization from dimethylformamide and water gave 117 g of 2-(4-cyclohexylphenyl)-6-fluoro3-methylquinoline-4-carboxylic acid, m.p. 316°-323°.

後処理

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 12 hours
  5. temperaturecooled
  6. customthe ethanol evaporated under reduced pressure
  7. dissolutionThe resulting solid was dissolved in water
  8. washwashed with ethyl ether
  9. filtrationThe resulting precipitate was filtered
  10. customdried
  11. customRecrystallization from dimethylformamide and water

出典と根拠

ORDレコード
ord-67bf7149f9d8498f9d6d8c65f83a5e1d
出典データセット
uspto-grants-1991_07
特許番号
US05032597

反応ノート

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