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Ethyl 1-(6-t-butylamino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate → 5-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368507
ノート
印刷プレビュー

反応式

HRID 368507 の反応式
C([NH:5][C:6]1[N:11]=[C:10]([N:12]2[C:21]3[C:16](=[C:17]([N+:25]([O-])=O)[C:18]([F:24])=[C:19]([F:23])[C:20]=3[Cl:22])[C:15](=[O:28])[C:14]([C:29]([O:31]CC)=[O:30])=[CH:13]2)[C:9]([F:34])=[CH:8][C:7]=1[F:35])(C)(C)C>[Fe].C(O)=O>[NH2:25][C:17]1[C:18]([F:24])=[C:19]([F:23])[C:20]([Cl:22])=[C:21]2[C:16]=1[C:15](=[O:28])[C:14]([C:29]([OH:31])=[O:30])=[CH:13][N:12]2[C:10]1[C:9]([F:34])=[CH:8][C:7]([F:35])=[C:6]([NH2:5])[N:11]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 22121269Ethyl 1-(6-t-butylamino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

生成物 1

HCID 221211655-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid収率 83.6%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 284Formic Acid溶媒

反応条件

温度
85 °C

実験手順

To 10 ml of formic acid was added 960 mg of ethyl 1-(6-t-butylamino-3,5-difluoropyridine-2-yl)-8-chloro-6,7-difluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate together with 1.0 g of iron powder, and the mixture was stirred at 80 to 90° C. for 5 hours and 40 minutes. The insoluble content was separated by filtration through celite, and the content separated by the celite and the celite were washed with formic acid and chloroform. The filtrate and the washings were concentrated under reduced pressure. To the residue was added the 6 ml of the mixed solution of 4N hydrochloric acid and acetic acid (1:1), and the mixture was heated under reflux for 2 hours with stirring and allowed to cool. The precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 625 mg of the title compound as a yellow powder.

後処理

  1. customThe insoluble content was separated by filtration through celite
  2. customthe content separated by the celite
  3. washthe celite were washed with formic acid and chloroform
  4. concentrationThe filtrate and the washings were concentrated under reduced pressure
  5. additionTo the residue was added the 6 ml of the mixed solution of 4N hydrochloric acid and acetic acid (1:1)
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 2 hours
  8. stirringwith stirring
  9. temperatureto cool
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with ethanol and diisopropylether successively

出典と根拠

ORDレコード
ord-58445e950ec544d5a3eb0e9c2dd5e867
出典データセット
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06133284

反応ノート

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