Potassium Carbonate → HCID 20028916, compound

HRID 1722567Notes

Reaction equation

HRID 1722567 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.I[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([N:5]1[CH:6]=[CH:7][C:2](=[O:1])[CH:3]=[CH:4]1)[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178418642HCID 178418642, compound

Product 1

HCID 20028916HCID 20028916, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The starting material may be prepared as follows: A solution of 4-hydroxypyridine (950 mg.) and 1-iodopropane (2.34 ml.) in acetone (30 ml.) was stirred under reflux for 2 hours with powdered potassium carbonate (2.76 g.). The reaction mixture was cooled to room temperature and filtered. The solvent was evaporated from the filtrate and the residue was purified by chromoatograph on Kieselgel 60 (100 g.) eluting with methylene chloride/MeOH 100:0 to 80:20 v/v to give 1-n-propyl-4-pyridone (1.05 g.), an oil having n.m.r. in CDCl3 :-0.9(t, 3H); 1.75(m, 2H9; 3.7(t, 2H); 6.23(d, 2H); 7.28(d, 2H). This material was chlorinated as described in the second part of Example 56 to give 4-chloro-1-n-propylpyridinium toluene-p-sulphonate.

Workup

  1. customThe starting material may be prepared
  2. filtrationfiltered
  3. customThe solvent was evaporated from the filtrate
  4. customthe residue was purified by chromoatograph on Kieselgel 60 (100 g.)
  5. washeluting with methylene chloride/MeOH 100:0 to 80:20 v/v

Sources & evidence

ORD record
ord-5f601a5ba4d24a5f883dfbac97f90b4a
Source dataset
uspto-grants-1989_08
Patent number
US04855420

Reaction notes

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