Phosphorus oxychloride → 4-Chloro-nicotinonitrile

HRID 506147Notes

Reaction equation

HRID 506147 reaction equation
COC1C=C(C=CC=1OC)C[N:7]1[CH:12]=[CH:11][C:10](=O)[C:9]([C:14]#[N:15])=[CH:8]1.[Li+].[Cl-].O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:10]1[C:9]([C:14]#[N:15])=[CH:8][N:7]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 433294Lithium ChlorideHCID 684661431-(3,4-Dimethoxybenzyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile

Product 1

HCID 134111124-Chloro-nicotinonitrile

Procedure

Alternatively, as shown in Scheme 3 below, the bisdimethylaminemethylene intermediate iii obtained by reaction of 3-oxo-butyronitrile ii with DMF-DMA can be reacted with 3,4-dimethoxybenzylamine at reflux in a solvent such as toluene to give 1-(3,4-dimethoxybenzyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile viii. Reaction of viii with excess LiCl in refluxing POCl3 results in removal of the dimethoxybenzyl group and conversion to the corresponding 4-chloro-nicotinonitrile v.

Sources & evidence

ORD record
ord-a8bc9026c88149f59cba0ddf56555047
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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