Ammonia → 4-Quinolone-3-carboxylic acid

HRID 373531ノート

反応式

HRID 373531 の反応式
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]

参加物

3

反応物 2

HCID 222AmmoniaHCID 14880212HCID 14880212、化合物

生成物 1

HCID 2208754-Quinolone-3-carboxylic acid

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8b2393fe83cc4d5ab8ecaaeccdb5f714
出典データセット
uspto-grants-1992_11
特許番号
US05164392

反応ノート

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