Nicotinamide → 2-Chloronicotinonitrile

HRID 1488723Notes

Reaction equation

HRID 1488723 reaction equation
C(C1C=CC=CN=1)#N.[C:9]([NH2:17])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:19]>>[Cl:19][C:11]1[C:10]([C:9]#[N:17])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 936NicotinamideHCID 7522Pyridine-2-carbonitrileHCID 24819Phosphorus pentachloride

Product 1

HCID 810792-ChloronicotinonitrileYield 30%

Procedure

For production of a cyanopyridine, there has been known, for example, a process which comprises reacting nicotinamide with phosphorus pentachloride to obtain 2-chloro-3-cyano-pyridine at a yield of 30% [Org. Syn., Coll., Vol. IV, p. 166 (1963)]. In this process, however, use of phosphorus pentachloride makes the operation troublesome; the conversion of acid amide group into nitrile group and the chlorination of ring proceed simultaneously, perchlorides are formed, and various side reactions take place; thus, the yield of intended product is not sufficient. Hence, the process has not been satisfactory for selective production of an intended cyanopyridine.

Sources & evidence

ORD record
ord-184d90898bac4d0eb764b0c08a354c75
Source dataset
uspto-grants-1997_10
Patent number
US05675012

Reaction notes

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