Water → Clinafloxacin

HRID 1450684

反応式

HRID 1450684 の反応式
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([Cl:18])=[C:16]3[C:11]([C:12](=[O:25])[C:13]([C:22]([OH:24])=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:21][CH2:20]3)=[CH:10][C:9]=2[F:26])[CH2:4]1.O.[OH-].[Na+]>CO>[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([Cl:18])=[C:16]3[C:11]([C:12](=[O:25])[C:13]([C:22]([OH:24])=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:20][CH2:21]3)=[CH:10][C:9]=2[F:26])[CH2:4]1

参加物

5

反応物 3

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 600623-Quinolinecarboxylic acid, 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, hydrochloride (1:1)2 回

生成物 1

HCID 60063Clinafloxacin収率 91.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
60 °C

実験手順

To a 1-liter flask was charged 100 g (0.27 mol) 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid monohydrochloride followed by 200 mL methanol and 200 mL demineralized water. The mixture was stirred and heated to 60° C. where it was maintained until solution was achieved. To a separate 1-liter flask was added 0.5 g Ca(OH)2 and 200 mL demineralized water and the mixture stirred and heated to 60° C. To this mixture was simultaneously added the solution containing the 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3carboxylic acid monohydrochloride in aqueous methanol while at the same time charging 5% w/w NaOH at such a rate to maintain the pH between 7.5 and 8.0. When the addition was complete, the mixture was stirred and cooled to 25° C. over 1 hour and filtered on a 4 inch Buchner funnel (filtration time: 38 seconds) and the solid washed with 200 mL demineralized water to give a wet cake. The cake was vacuum dried to give 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as a white solid (90 g).

後処理

  1. temperaturewas maintained until solution
  2. stirringthe mixture stirred
  3. temperatureheated to 60° C
  4. additionTo this mixture was simultaneously added the solution
  5. temperatureto maintain the pH between 7.5 and 8.0
  6. additionWhen the addition
  7. stirringthe mixture was stirred
  8. temperaturecooled to 25° C. over 1 hour
  9. filtrationfiltered on a 4 inch Buchner funnel (filtration time: 38 seconds)
  10. washthe solid washed with 200 mL
  11. customto give a wet cake
  12. customdried

出典と根拠

ORDレコード
ord-0c6130124afb4f9eaf9d35ba41938f7a
出典データセット
uspto-grants-1997_02
特許番号
US05602254

関連ノート

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