Dimethylcarbamoyl Chloride → 3-Methyl-1-dimethylcarbamoyloxypyridinium chloride

Reaction equation

[CH3:1][C:2]1[CH:3]=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][N:10]([CH3:14])[C:11]([Cl:13])=[O:12]>>[Cl-:13].[CH3:1][C:2]1[CH:3]=[N+:4]([O:8][C:11](=[O:12])[N:10]([CH3:14])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 6598Dimethylcarbamoyl Chloride

HCID 138583-Picoline-N-oxide

Product 1

HCID 132499833-Methyl-1-dimethylcarbamoyloxypyridinium chloride

Procedure

Also, Fife et al., cited hereabove and Heterocycles 22:93-96(1984), reported the reaction of 3-methylpyridine-1-oxide with dimethyl-carbamoyl chloride to give 3-methyl-1-dimethylcarbamoyloxypyridinium chloride. Reaction of this pyridinium salt with potassium cyanide in water gave 3-methyl-2-cyanopyridine (89%) and the 6-isomer (11%).

Sources & evidence

ORD record: ord-0ef46d27beeb4da4ad834a52dd0556e3
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04843163

Reaction notes

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