Ammonia → 4-Quinolone-3-carboxylic acid

HRID 373531노트

반응식

HRID 373531 반응식
C1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10](F)=[C:11](N4C[C@H](C)N[C@H](C)C4)[CH:12]=3)[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)CC1.N>>[O:24]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][CH:5]=[C:6]1[C:25]([OH:27])=[O:26]

참가 물질

3

반응물 2

HCID 222AmmoniaHCID 14880212HCID 14880212, 화합물

생성물 1

HCID 2208754-Quinolone-3-carboxylic acid

실험 절차

In a sealed tube, 1-cyclopropyl-5,6-difluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 28% aqueous ammonia were heated at 100° C. for 48 hours. The reaction mixture was concentrated under reduced pressure. A 1N aqueous solution of sodium hydroxide was added to the residue, and the insoluble matter was removed by filtration. A 10% aqueous solution of acetic acid was added to the filtrate to adjust its pH to 8, and it was then extracted with chloroform. The extract was dried and concentrated. Acetonitrile was added to the residue, and the mixture was cooled with ice. The crystals were collected by filtration and recrystallized from aqueous ammonia to give 5-amino-1-cyclopropyl-6-fluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid m p. 253°-254° C.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionA 1N aqueous solution of sodium hydroxide was added to the residue
  3. customthe insoluble matter was removed by filtration
  4. additionA 10% aqueous solution of acetic acid was added to the filtrate
  5. extractionwas then extracted with chloroform
  6. customThe extract was dried
  7. concentrationconcentrated
  8. additionAcetonitrile was added to the residue
  9. temperaturethe mixture was cooled with ice
  10. filtrationThe crystals were collected by filtration
  11. customrecrystallized from aqueous ammonia

출처 및 근거

ORD 기록
ord-8b2393fe83cc4d5ab8ecaaeccdb5f714
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05164392

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