Stannous Chloride → 6-Aminoquinoline-8-carboxylic acid

HRID 1756500노트

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HRID 1756500 반응식
[C:1]([C:4]1[CH:5]=[C:6]([N+:14]([O-])=O)[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([OH:3])=[O:2].Cl[Sn]Cl>CO>[NH2:14][C:6]1[CH:7]=[C:8]2[C:13](=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=1)[N:12]=[CH:11][CH:10]=[CH:9]2

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 1501526-Nitro-8-quinolinecarboxylic acid

생성물 1

HCID 193905666-Aminoquinoline-8-carboxylic acid수율 35.5%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
40 °C

실험 절차

To a suspension of 8-carboxy-6-nitroquinoline (4 g; 18 mM) in methanol (70 ml) was added SnCl2 (20.4 g; 90 mM). The mixture was heated to, and maintained at 40° C. until dissolution of the insoluble. After evaporation of the :solvent, the residue was taken-up in a 2M aqueous solution of NaOH and purified by subjecting to chromatography on Dowex 1X2 Resin. After basification (pH3) with concentrated NH4OH the resulting solid was further purified by subjecting to chromatography on HP20SS resin, eluting with MeOH/H2O--AcOH 1% (30.70) to give 6-amino-8-carboxyquinoline (1.2 g, 35.5%)

후처리

  1. temperatureThe mixture was heated to, and
  2. customAfter evaporation of the :solvent
  3. custompurified
  4. customAfter basification (pH3) with concentrated NH4OH the resulting solid was further purified
  5. washeluting with MeOH/H2O--AcOH 1% (30.70)

출처 및 근거

ORD 기록
ord-82ce28bcf4454b319a82060f12018710
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05441949

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