Stannous Chloride → HCID 19390591, compound

HRID 1756503Notes

Reaction equation

HRID 1756503 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([N+:17]([O-])=O)[CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:6])[CH:2]=[CH2:3].Cl[Sn]Cl>CO>[NH2:17][C:15]1[CH:16]=[C:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 193905822-Propen-1-yl 8-nitro-6-quinolinecarboxylate

Product 1

HCID 19390591HCID 19390591, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 6-allyloxycarbonyl-8-nitroquinoline (4 g; 15.5 mM) in methanol (80 ml) was added SnCl2. (17.8 g-77.5 mM). The mixture was heated at 40° C. for 1 hour. After evaporation of the solvent, the residue was partitioned between an aqueous solution of NaHCO3 (10%) and ethyl acetate. The organic phase was concentrated and purified by subjecting to flash chromatography, eluting with ethylacetate/petroleum ether (30/70) to give 8-amino-6-allyloxycarbonylquinoline (3.4 g; 96%).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between an aqueous solution of NaHCO3 (10%) and ethyl acetate
  3. concentrationThe organic phase was concentrated
  4. custompurified
  5. washeluting with ethylacetate/petroleum ether (30/70)

Sources & evidence

ORD record
ord-90a86ea5f20b49d0b6f7d1f9fc424a1f
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

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