Sodium Azide → HCID 86038331, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 6-aminopyridine-2-carboxylate 1-oxide hydrochloride (Intermediate 122, 3.34 g, 16 mmol) was dissolved in 10% HCl (aqueous) and cooled to 5° C. An aqueous solution of NaNO2 (1.5 g, 21 mmol) was added dropwise maintaining temperature below 5° C. After 15 minutes of stirring, an aqueous solution of NaN3 (1.4 g, 21 mmol) was added dropwise maintaining temperature below 5° C. The reaction was stirred at 5° C. for 30 minutes and slowly warmed to room temperature. The product was extracted with DCM and then the aqueous layer was basified (with 50% NaOH to pH 13) and then extracted again with DCM. Drying (MgSO4) and removal of solvent yielded a yellow oil (2.6 g, 82%).

Provenance & Evidence