Potassium Carbonate → 2-(4-Aminophenylthio)quinoline

HRID 2395317Notes

Reaction equation

HRID 2395317 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 145104-Aminothiophenol

Product 1

HCID 226371302-(4-Aminophenylthio)quinolineYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloroquinoline (0.04 moles, 6.54 g), 4-aminothiophenol (0.04 moles, 5.0 g) and potassium carbonate (0.04 moles, 5.52 g) were stirred at room temperature in 200 ml of ethanol for 18 hr. The reaction mixture was concentrated, ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with ethyl acetate/hexane to yield 2-(4-aminophenylthio)quinoline 4.0 g, 40%. Mass Spec (FD) 252. Calculated for C15H12N2S: C, 71.40; H, 4.79, N, 11.10. Found: C, 71.11; H, 4.98N, 11.20.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added
  3. washthe solution washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified by HPLC over silica gel
  7. washeluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-187d8c6a3de84140b02930009d25c0b5
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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