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 561153ノート

反応式

HRID 561153 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6066176957904da8aa7a3b8384ac0277
出典データセット
uspto-grants-2011_11
特許番号
US08063221B2

反応ノート

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