Ethanol → 7-(1-Piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1292

反応式

HRID 1292 の反応式
[N:1]1([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:25])[C:12]([C:20]([O:22]CC)=[O:21])=[CH:13][N:14]3[CH:17]3[CH2:19][CH2:18]3)=[C:9]([CH3:26])[C:8]=2[F:27])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[Na+].C(O)C>O>[N:1]1([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:25])[C:12]([C:20]([OH:22])=[O:21])=[CH:13][N:14]3[CH:17]3[CH2:18][CH2:19]3)=[C:9]([CH3:26])[C:8]=2[F:27])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15345961Ethyl 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

生成物 1

HCID 146511667-(1-Piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid収率 56.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To ethyl 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (23 mg) are added 10% aqueous solution of sodium hydroxide (3 ml) and ethanol (3 ml), and the mixture is refluxed for 1 hour. After cooling, the reaction mixture is diluted with water and washed with dichloromethane. After the aqueous layer is made acidic with acetic acid and then made weak alkaline with an aqueous sodium hydrogen carbonate. The resultant is extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure and to the residue is added ethanol. The precipitated crystals are filtered and recrystallized from dimethylformamide to give 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (12 mg), as white powder, m.p. 231°-233° C.

後処理

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. washwashed with dichloromethane
  4. extractionThe resultant is extracted with dichloromethane
  5. customthe extract is dried
  6. distillationThe solvent is distilled off under reduced pressure and to the residue
  7. additionis added ethanol
  8. filtrationThe precipitated crystals are filtered
  9. customrecrystallized from dimethylformamide

出典と根拠

ORDレコード
ord-cf9ee368bd9548f6bc7d6beba130ae9b
出典データセット
uspto-grants-1998_03
特許番号
US05723648

関連ノート

読み込み中…