Chlorotrimethylsilane → Methyl 5-cyano-6-methoxypyridine-2-carboxylate

HRID 1761455Notes

Reaction equation

HRID 1761455 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:11]([OH:13])=[O:12])=[N:7][C:8]=1[O:9][CH3:10])#[N:2].[CH3:14][Si](C)(C)Cl>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:11]([O:13][CH3:14])=[O:12])=[N:7][C:8]=1[O:9][CH3:10])#[N:2]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 136501045-Cyano-6-methoxypicolinic acid

Product 1

HCID 21241774Methyl 5-cyano-6-methoxypyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Cyano-6-methoxypyridine-2-carboxylic acid (see above) is reacted in methanol with the help of trimethylchlorosilane to give methyl 5-cyano-6-methoxypyridine-2-carboxylate (m.p. 125°-125° C.). Subsequent hydrogenation in methanol on palladium/charcoal in the presence of hydrochloride acid gives the desired aminomethyl compound (m.p. of the hydrochloride: 224°-226° C.). By the addition of a few drops of triethanolamine, the hydrogenation solution is brought to a pH of 7 and used directly for the following reaction.

Sources & evidence

ORD record
ord-41281543d4c542d098d966f6504adf37
Source dataset
uspto-grants-1989_05
Patent number
US04826858

Reaction notes

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