Cyanide → 4-Cyanopyridine

HRID 1905457Notes

Reaction equation

HRID 1905457 reaction equation
COS([O-])(=O)=O.[CH3:7][C:8]1[CH:9]=[N+:10](OC)[CH:11]=[CH:12][CH:13]=1.[C-:16]#[N:17]>>[CH3:7][C:8]1[C:9]([C:16]#[N:17])=[N:10][CH:11]=[CH:12][CH:13]=1.[C:16]([C:13]1[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=1)#[N:17]

Participants

4

Reactant 2

HCID 5975CyanideHCID 22168441HCID 22168441, compound

Product 2

HCID 75064-CyanopyridineHCID 8199283-Methylpyridine-2-carbonitrile

Procedure

It has been reported by Fife et al., Heterocycles 22:1121-4(1984) that 3-methyl-1-methoxypyridinium methylsulfate reacted with cyanide ion to give 3-methyl-2-cyanopyridine and "high percentages" of the 4-cyanopyridine isomer. In Table 1 on page 1122, Fife et al. reported that the 4-cyano compound was gobtained in 69% yield and 3-methyl-2-cyanopyridine was obtained in 24% yield.

Sources & evidence

ORD record
ord-e20f50c5acee44ae99940512b8ec0dd6
Source dataset
uspto-grants-1989_06
Patent number
US04843163

Reaction notes

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