Diethyl Ether → 2-[4-(Dimethylamino)styryl]-1-dodecylpyridinium bromide

Participants

Reaction Steps

4-Picoline (2.79 g, 0.03 mole) and 1-bromohexane (4.25 ml, 0.03 mole) were heated in an oil bath at 130° C. for 2 hours. The resulting brown oil was cooled. Methanol (40 ml), 4-dimethylaminobenzaldehyde (4.5 g, 0.03 mole) and piperdine (0.25 ml) were added. The mixture was refluxed for 3 hours and cooled. A large volume of ether was added to form a crystalline product which was recrystallised by dissolving in isopropyl alcohol and adding ether to give crystals of 4-[4-(dimethylamino)styryl]-1-hexylpyridinium bromide quarter hydrate (2.2 g), melting point 224°-226° C. (decomposition). The compound exhibited infra-red spectral bands at 720, 815, 835, 883, 940, 987, 1158, 1330, 1362, 1522, 1575 and 1640 wavenumbers.

Provenance & Evidence