Methanol → Ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate

HRID 1458006ノート

反応式

HRID 1458006 の反応式
[F:1][C:2]1[C:3]([N+:24]([O-])=O)=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[F:12])[N:8]([C@@H:14]1[CH2:16][C@@H:15]1[F:17])[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].CO>[Ni].O1CCOCC1>[NH2:24][C:3]1[C:2]([F:1])=[C:11]([F:12])[C:10]([CH3:13])=[C:9]2[C:4]=1[C:5](=[O:23])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][N:8]2[C@@H:14]1[CH2:16][C@@H:15]1[F:17]

参加物

5

反応物 2

HCID 887MethanolHCID 11014105Ethyl 6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate

生成物 1

HCID 11759598Ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate収率 98%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 312751,4-Dioxane溶媒

実験手順

A 3.91 g (37.6 mmol) portion of ethyl 6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate was suspended in 1 liter of a 1:1 mixture of methanol and 1,4-dioxane. This was mixed with 200 ml of Raney nickel and stirred for 10 minutes at room temperature. After completion of the reaction, the reaction solution was filtered and the resulting filtrate was concentrated. The resulting residue was dissolved in 300 ml of chloroform and filtered through celite. By concentrating the filtrate, 12.5 g (98%) of the title compound was obtained.

後処理

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. concentrationthe resulting filtrate was concentrated
  4. dissolutionThe resulting residue was dissolved in 300 ml of chloroform
  5. filtrationfiltered through celite
  6. concentrationBy concentrating the filtrate

出典と根拠

ORDレコード
ord-cb898df2daa646feabb8b9f7f2dea8ba
出典データセット
uspto-grants-1998_12
特許番号
US05849757

反応ノート

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