Potassium Carbonate → HCID 20028916, compound

HRID 2118593Notes

Reaction equation

HRID 2118593 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 chromatography on Kieselgel 60 (100 g.) eluating 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, 2H); 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 chromatography on Kieselgel 60 (100 g.)

Sources & evidence

ORD record
ord-133cd7f112644916a365609025cd5fae
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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