Delta-Valerolactone → 8-chloro-2-methyl-2,3,4,4a-tetrahydro-10H-1,2-oxazino(3,2-b)(1,3)benzoxazin-10-one

Participants

Reaction Steps

A mixture of 30 g. of γ -valerolactone, 30 ml. of distilled thionyl chloride and 0.5 g. of zinc chloride was heated on a steam bath overnight and then distilled at 15 mm. The distillate was redistilled at 69- 70° and 15 mm. giving 34 g. of 4-chlorovaleryl chloride. The acid chloride was reduced catalytically, reacted with 5-chlorosalicylhydroxamic acid and the resulting intermediate was ring-closed according to the method described in Example 3. The product after recrystallization from trichloroethylene weighed 8.5 g. and melted at 210- 213° C.

Provenance & Evidence