Methanamine, N-methoxy-, hydrochloride (1:1) → 5-hydroxy-N-methoxy-N-methylpicolinamide

HRID 626197Notes

Reaction equation

HRID 626197 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][O:14][CH3:15]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:10])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2687405-Hydroxypyridine-2-carboxylic acid

Product 1

HCID 866889815-hydroxy-N-methoxy-N-methylpicolinamideYield 52%

Procedure

Following the same procedure as described in example 41, step A, 5-hydroxypicolinic acid (6.2 g, 1.0 eq) was reacted with N,O-dimethylhydroxylamine hydrochloride (5.2 g, 1.2 eq) to get the desired product with column chromatography (4.25 g, 52% yield).

Sources & evidence

ORD record
ord-5f8d3be2ff6b4f199e74c6d5fd395dfc
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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