4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium → 4-Methoxy-2,3,5-trimethylpyridine 1-oxide

HRID 2231953Notes

Reaction equation

HRID 2231953 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].[CH3:12][O-:13].[Na+]>>[CH3:12][O:13][C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-:9])=[C:4]([CH3:10])[C:3]=1[CH3:11]

Participants

3

Reactant 2

HCID 27791414-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-iumHCID 10942334Sodium Methoxide

Product 1

HCID 107022374-Methoxy-2,3,5-trimethylpyridine 1-oxideYield 92%

Procedure

0.86 g (5 mmol) 4-chloro-2,3,5-trimethylpyridine N-oxide and 8.5 ml 2M sodium methoxide was heated in a closed vessel to 70° C. for 16 hrs. Gave after work up 92% yield of 4-methoxy-2,3,5-trimethylpyridine N-oxide. Addition of 20% dimethylsulfoxide to the solvent increases the reaction rate but complicates the work up. The product was obtained as a waxy solid. NMR: 2×3H, 2,25; 3H, 2,5(s); 3H, 3,80(s); 1H, 8,2(s). (CDCl3).

Sources & evidence

ORD record
ord-0a4dfe32932d4bb3b908ed97491c6785
Source dataset
uspto-grants-1988_11
Patent number
US04785113

Reaction notes

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