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

HRID 864348

반응식

HRID 864348 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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. The aqueous layer is made acidic with acetic acid and then made weakly alkaline with an aqueous sodium hydrogen carbonate. The resultant product 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.

후처리

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. washwashed with dichloromethane
  4. extractionThe resultant product 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

출처 및 근거

ORD 기록
ord-5063992e1f1441dd8b4ab55f0201d1b1
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563138

연결된 노트

불러오는 중…