Sodium Hydroxide → 1-Chloro-4-methylpyridazino[4,5-b]indolizine

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Reaction Steps

The stirred suspension of the 4-methyl-2H-pyridazino[4,5-b]indolizine-1-one (10.0 g, 0.050 mole) in phosphoryl chloride (75 ml) was refluxed under nitrogen for 3 hours. After cooling, the reaction mixture was poured into ice-water (1 L) with vigorous stirring. Then, the solution was made alkaline (pH 8-9) by addition of a 50% W/W sodium hydroxide solution (cooling). The suspension was filtered and the solid was washed with water and dried to yield 1-chloro-4-methylpyridazino[4,5-b]indolizine (10.33 g). For analysis, a sample was recrystallized from dichloromethane and ether.

Provenance & Evidence