Potassium Carbonate → 4-(4-Nitrophenylthio)quinoline

HRID 2395326Notes

Reaction equation

HRID 2395326 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 158094-NitrobenzenethiolHCID 691404-Chloroquinoline

Product 1

HCID 189716424-(4-Nitrophenylthio)quinolineYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloroquinoline (32.3 mmoles, 5.2 g), 4-nitrothiophenol (32.3 mmoles, 5.0 g) and potassium carbonate (32.3 mmoles, 4.46 g) were stirred at room temperature in 500 ml of ethanol for 16 hr. The reaction mixture was then 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 20-40% ethyl acetate/hexane to yield 4-(4-nitrophenylthio)quinoline 4.9 g, 54%. Mass Spec (FD) 282. Calculated for C15H10N2O2S: C, 63.82H, 3.57N, 9.92. Found: C, 65.09; H, 3.81; N, 10.02.

Workup

  1. concentrationThe reaction mixture was then 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 20-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-75aaeb9b64054613a4dfec372f4a5617
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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