m-Chloroperbenzoic acid → Pyridine-2-carbonitrile

HRID 1164849Notes

Reaction equation

HRID 1164849 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.C[Si]([C:31]#[N:32])(C)C>>[C:31]([C:11]1[CH:10]=[CH:15][CH:14]=[CH:13][N:12]=1)#[N:32].[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:31]#[N:32])=[N:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 82115Trimethylsilyl cyanideHCID 104626053-(Diethoxyphosphorylmethyl)pyridine

Product 2

HCID 7522Pyridine-2-carbonitrileHCID 544899365-(Diethylphosphonomethyl)-2-cyanopyridine

Procedure

Treatment of 3-(diethylphosphonomethyl)pyridine (Biochemistry 19, 3400) with m-chloroperbenzoic acid followed by trimethylsilyl cyanide gives both 3-diethylphosphonomethyl)-2-cyanopyridine and 5-(diethylphosphonomethyl)-2-cyanopyridine, the starting materials for compounds under (a) and (b).

Sources & evidence

ORD record
ord-06c1dc439c2c43099412986739386ee8
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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