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

HRID 1458006노트

반응식

HRID 1458006 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb898df2daa646feabb8b9f7f2dea8ba
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849757

반응 노트

불러오는 중…