Pyridine → HCID 23456162, compound

Participants

Reaction Steps

A mixture of 2-chloro-5-chlorosulfonyl-3-methoxypyridine (0.65 g, 2.68×10-3 mole) (see Example 9), 4-amino-N,N-dioctadecyl-1-hydroxy-2-naphthamide (1.40 g, 1.98×10-3 mole) and pyridine (0.20 g, 2.5×10-3 mole) was stirred overnight at room temperature. Additional pyridine (7 drops) was employed after the first 21/2 hours of stirring. The reaction mixture was concentrated in vacuo and diluted with water to precipitate an oil which changed to a waxy solid upon trituration with water. The waxy solid was dissolved in toluene and purified by column chromatography on silica gel using toluene. The toluene fraction was concentrated to a solid which was recrystallized from ethanol; yield, 0.40 g (22 percent), m.p. 85° to 87° C.

Provenance & Evidence