Potassium Permanganate → 5-Cyano-6-methoxypicolinic acid

HRID 1761454Notes

Reaction equation

[C:1]([C:3]1[C:4]([O:10][CH3:11])=[N:5]C(C)=[CH:7][CH:8]=1)#[N:2].[Mn]([O-])(=O)(=O)=O.[K+].[CH:18]([OH:21])([CH3:20])C.[OH2:22].Cl>>[C:1]([C:3]1[CH:8]=[CH:7][C:20]([C:18]([OH:21])=[O:22])=[N:5][C:4]=1[O:10][CH3:11])#[N:2]

Participants

Reactant 3

HCID 516875Potassium Permanganate

HCID 53238032-Methoxy-6-methylnicotinonitrile

HCID 21409480Isopropanol-hcl-water

Product 1

HCID 136501045-Cyano-6-methoxypicolinic acid

Procedure

3-Cyano-2-methoxy-6-methylpyridine is oxidised with potassium permanganate in aqueous solution to give 5-cyano-6-methoxypyridine-2-carboxylic acid (m.p. 235°-237° C.), subsequent hydrogenation of which on palladium/charcoal in isopropanol/water/hydrochloric acid gives the desired compound.

Sources & evidence

ORD record: ord-265e4db7ac3141999db4c614009fc41b
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04826858

Reaction notes

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