Potassium Carbonate → HCID 59983193, compound

HRID 1643879Notes

Reaction equation

HRID 1643879 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[C:15]([F:18])([F:17])[F:16].O.O.Cl[Sn]Cl.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([NH2:12])=[C:5]2[C:15]([F:17])([F:16])[F:18]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 61436Stannous chloride dihydrateHCID 22595772HCID 22595772, compound

Product 1

HCID 59983193HCID 59983193, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 6-chloro-3-nitro-4-(trifluoromethyl)quinoline (5.53 g, 20 mmol) (prepared according to the procedures described by Tarby, C. M., in WO 2003062238) in EtOAc (100 mL) was added SnCl2.2H2O (18 g, 80 mmol). The resulting mixture was stirred at RT for 18 h, then at 80° C. for 6 h. After cooling to RT, saturated aqueous K2CO3 (5 mL) was added. The reaction mixture was stirred at RT for 30 min, and then solid K2CO3 (16.6 g, 120 mmol) was added stirring was continued at RT for 4 more hours. EtOAc (200 mL) was added, the resulting mixture was filtered, and the filtrate concentrated in vacuo to give the title compound (4.8 g, 97% yield) as an off-white solid.

Workup

  1. waitat 80° C. for 6 h
  2. temperatureAfter cooling to RT
  3. stirringThe reaction mixture was stirred at RT for 30 min
  4. stirringstirring
  5. customwas continued at RT for 4 more hours
  6. filtrationthe resulting mixture was filtered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-a17a6779fea54a999898f186bb0b7cf4
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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