Stannous Chloride → HCID 19390566, compound

HRID 1756500Notes

Reaction equation

HRID 1756500 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 19390566HCID 19390566, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

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%)

Workup

  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)

Sources & evidence

ORD record
ord-82ce28bcf4454b319a82060f12018710
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

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