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Ethyl formate → 1-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinoline

HRID 1073760
ノート
印刷プレビュー

反応式

HRID 1073760 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:22])[C:10]([F:21])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH:16]([CH3:20])[CH2:15]4)[CH:12]=3)[C:7](=[O:23])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[CH3:24][O-:25].[Na+].[CH:27](OCC)=[O:28]>ClCCl>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:22])[C:10]([F:21])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH:27]=[O:28])[CH:16]([CH3:20])[CH2:15]4)[CH:12]=3)[C:7](=[O:23])[CH:6]([CH:24]=[O:25])[CH2:5]2)[CH2:2][CH2:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 157127231-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)5-methyl-4-oxo-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 157127251-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinoline収率 65.6%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)5-methyl-4-oxo-1,2,3,4-tetrahydroquinoline (5.7 g) is dissolved in dichloromethane (200 ml) and thereto is added gradually sodium methylate (6.8 g) and further added dropwise a solution of ethyl formate (9.3 g) in dichloromethane (100 ml). The mixture is stirred at room temperature for one hour and then refluxed for one hour. After cooling, the reaction mixture is washed with water (200 ml) and dilute aqueous sodium hydroxide solution (200 ml) and extracted. The aqueous layer is taken and is made weakly acidic with diluted hydrochloric acid and extracted with dichloromethane. The extract is washed with water, dried and then dichloromethane is distilled off. The resulting residue is purified by silica gel column chromatography (eluent, chloroform) and recrystallized from diethyl ether - isopropanol to give 1-cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinoline (4.4 g) as yellow powdery crystals, m.p. 148°-150° C.

後処理

  1. temperaturerefluxed for one hour
  2. temperatureAfter cooling
  3. washthe reaction mixture is washed with water (200 ml) and dilute aqueous sodium hydroxide solution (200 ml)
  4. extractionextracted
  5. extractionextracted with dichloromethane
  6. washThe extract is washed with water
  7. customdried
  8. distillationdichloromethane is distilled off
  9. customThe resulting residue is purified by silica gel column chromatography (eluent, chloroform)
  10. customrecrystallized from diethyl ether - isopropanol

出典と根拠

ORDレコード
ord-db1329f4e4fa437faccb6f58cc25cfeb
出典データセット
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04971970

反応ノート

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