Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxo-2-phenylquinoline-3-carboxylate → Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate

HRID 561153노트

반응식

HRID 561153 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-])=O)[C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:5]2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:3][CH2:2]1>CC(O)=O.[Fe]>[NH2:18][C:9]1[C:10]([F:17])=[C:11]([F:16])[C:12]([O:14][CH3:15])=[C:13]2[C:8]=1[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:5]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[N:4]2[CH:1]1[CH2:2][CH2:3]1

참가 물질

4

반응물 1

HCID 59002827Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxo-2-phenylquinoline-3-carboxylate

생성물 1

HCID 59002984Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate수율 102.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

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온도
90 °C

실험 절차

A suspension of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxo-2-phenylquinoline-3-carboxylate (1.05 g, 2.36 mmol) and iron powder (793 mg, 14.2 mmol) in AcOH (25 mL) was stirred at 90° C. for 3 h. After the reaction mixture was concentrated in vacuo, water was added and the crude product was extracted with EtOAc, washed with saturated aq. NaHCO3 and brine, dried over MgSO4. The solvent was removed in vacuo and the residue was dried to yield ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate (1.00 g, quant.) as a yellow amorphous solid.

후처리

  1. concentrationAfter the reaction mixture was concentrated in vacuo, water
  2. additionwas added
  3. extractionthe crude product was extracted with EtOAc
  4. washwashed with saturated aq. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residue was dried

출처 및 근거

ORD 기록
ord-6066176957904da8aa7a3b8384ac0277
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063221B2

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