Tin tetrachloride → HCID 86600792, compound

Reaction equation

[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[N:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.[Sn](Cl)(Cl)(Cl)Cl>Cl>[ClH:5].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][NH2:1])=[CH:10][N:11]=1

Participants

Procedure

An aqueous sodium nitrite solution (3.49 g of sodium nitrite in 12.5 mL of water) was dropwise added to a solution of 6-chloropyridine-3-amine (5.00 g) in hydrochloric acid (77.8 mL) over 10 minutes (such that the temperature does not exceed −20° C.) under dry ice-acetone cooling (−20 to −40° C.), followed by stirring under the same conditions for 1 hour. A solution of tin chloride (14.8 g) in hydrochloric acid (25 mL) was dropwise added thereto over 15 minutes, followed by stirring at approximately 0° C. for 2 hours. The precipitated solid was collected by filtration (washed with water and n-hexane) and was vacuum dried at 40° C. to yield the title compound (9.45 g, brown solid).