Stannous chloride dihydrate → HCID 19390586, compound

HRID 1756507Notes

Reaction equation

HRID 1756507 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:17]([O-])=O)[CH:13]=2)[N:8]=1)=[O:6])[CH:2]=[CH2:3].O.O.Cl[Sn]Cl>CO>[CH2:1]([O:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=2)[N:8]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 19390567HCID 19390567, compound

Product 1

HCID 19390586HCID 19390586, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-allyloxycarbonyl-6-nitroquinoline (1.25 g; 4.8 mM) in MeOH (20 ml) was added SnCl2.2H2O (7.65 g, 33.6 mM). After stirring at ambient temperature for 3 hours, the mixture was evaporated to dryness and the residue partitioned between an aqueous solution of NH4OH (pH 8.5) and ethyl acetate. The organic phase was concentrated and purified by subjecting to flash chromatography, eluting with ethyl acetate/petroleum ether (65/35) to give 2-allyloxycarbonyl-6-aminoquinoline (280 mg; 28%).

Workup

  1. customthe mixture was evaporated to dryness
  2. customthe residue partitioned between an aqueous solution of NH4OH (pH 8.5) and ethyl acetate
  3. concentrationThe organic phase was concentrated
  4. custompurified
  5. washeluting with ethyl acetate/petroleum ether (65/35)

Sources & evidence

ORD record
ord-260a0709056745d79a11cc38de02b69e
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

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