Water → HCID 20028878, compound

HRID 2118617Notes

Reaction equation

HRID 2118617 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1)([O-:5])=[O:4].O.[ClH:15].CC[O:18][CH2:19][CH3:20]>CS(C)=O.CCOCC>[ClH:15].[Cl:15][C:8]1[CH:7]=[CH:6][N:3]=[CH:20][C:19]=1[O:18][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 10953452Ether hydrochloride

Product 1

HCID 20028878HCID 20028878, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

The starting material was prepared by reaction of 4-nitro-3-hydroxy pyridine-N-oxide with acetyl chloride under reflux for 1 hour. The crude product was purified by rapid chromatography on silica gel using CH2Cl2 /MeOH 7:3 v/v as eluant to give 4-chloro-3-hydroxypyridine-N-oxide. Reduction of this compound with Raney nickel and hydrogen at ambient temperature for 2 hours in MeOH gave 4-chloro-3-hydroxypyridine. This compound was reacted with NaH in DMSO at 50°, the reaction mixture cooled and treated with 4-nitrobenzyl bromide for 1 hour. The reaction mixture was worked up with water and ether and the product treated with HCl/ether to give 4-chloro-3-(4-nitrobenzyloxy)pyridine hydrochloride. Reaction of the free base with excess methyl iodide at ambient temperature for 24 hours gave 4-chloro-1-methyl-3-(4-nitrobenzyloxy)pyridinium iodide. n.m.r. in d6DMSO: 4.35(s, 3H); 5.6(s, 2H); 7.7(d, 2H); 8.3(d, 2H); 8.4(d, 1 H); 8.7(d, 1H); 9.15(s, 1H).

Workup

  1. temperaturethe reaction mixture cooled

Sources & evidence

ORD record
ord-9893156637f248288ff22393bef70713
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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