Stannous chloride dihydrate → HCID 10131458, compound

HRID 1935172Notes

Reaction equation

HRID 1935172 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]#[N:15])=[C:7]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)([O-])=O.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]#[N:15])=[C:7]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 9924935HCID 9924935, compound

Product 1

HCID 10131458HCID 10131458, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.0 g (16.8 mmol) of 6-nitro-4-(3-trifluoromethylphenylamino)quinoline-3-carbonitrile and 18.9 g (83.8 mmol) of SnCl2.2H2O in 240 mL of EtOH was refluxed under N2 for 1 hr. Ice water was added followed by NaHCO3 to pH 8. The mixture was stirred for 2 hr and then extracted with CHCl3. Darco was added and the extracts were filtered through anhyd MgSO4 and evaporated. The residue was filtered through silica gel with 10% MeOH in CHCl3. Solvent evaporation and drying in vacuo (40° C.) gave 4.87 g of 6-amino-4-(3-trifluoromethylphenylamino)quinoline-3-carbonitrile as a brown solid: mass spectrum (electrospray, m/e): M+H 329.1.

Workup

  1. temperaturewas refluxed under N2 for 1 hr
  2. extractionextracted with CHCl3
  3. additionDarco was added
  4. filtrationthe extracts were filtered through anhyd MgSO4
  5. customevaporated
  6. filtrationThe residue was filtered through silica gel with 10% MeOH in CHCl3
  7. customSolvent evaporation
  8. customdrying in vacuo (40° C.)

Sources & evidence

ORD record
ord-31a102297ba14c3ca9bfc7e65a8eec37
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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