Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → Ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate

HRID 328570ノート

反応式

HRID 328570 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].S(O[CH2:31][CH2:32][Cl:33])(C1C=CC(C)=CC=1)(=O)=O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:9]2[CH2:31][CH2:32][Cl:33])=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 24758Sodium hydrideHCID 345422Ethyl 7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate

生成物 1

HCID 13174336Ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate

反応条件

温度
100 °C

実験手順

To a mixture containing 23.4 g of ethyl 7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylate and 6.9 g of 65% sodium hydride was added 90g of 2-tosyloxyethyl chloride. The resulting mixture was heated at 100° C for 4 hours. After concentration to dryness, the residue was extracted with chloroform. The extract was washed with water, and dried over anhydrous sodium sulfate. The solvent was removed by the distillation to leave a solid which was recrystallized from ethanol to give ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate, m.p. 207.5°-209.5° C.

後処理

  1. concentrationAfter concentration to dryness
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by the distillation
  6. customto leave a solid which
  7. customwas recrystallized from ethanol

出典と根拠

ORDレコード
ord-c04490d568ec45cd938521fcc59bae22
出典データセット
uspto-grants-1977_04
特許番号
US04017622

反応ノート

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