3-Aminopyridine → HCID 22800660, compound

Participants

Reaction Steps

(S)-3-Methylthio-9-nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (6 g.) is added to a solution of 3-aminopyridine (3 g.) in pyridine (100 cc.). After 6 hours at a temperature of about 20° C., the mixture is concentrated to dryness under reduced pressure (25 mm. Hg). The residue is dissolved in a mixture consisting of methylene chloride (300 cc.) and water (200 cc.). The organic phase is decanted, washed with water (3 × 200 cc.), dried over magnesium sulphate, filtered and then concentrated to dryness. The residue obtained is recrystallised from acetonitrile (40 cc.) to give (S)-9-nitro-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (3.9 g.) in the form of white crystals melting at 144° C.

Provenance & Evidence