Tert-Butyl hypochlorite → 1,4-Phthalazinedione

Participants

Reaction Steps

To a solution of t-butyl hypochlorite (12.3 g., 0.12 m.) in acetone (500 ml.), which is cooled to -60°, is added the sodium salt of phthalhydrazide, (12.3 g., 0.067 m.). After 2.5 hours at -60° to -50°, the reaction mixture is filtered to give a solution of 1,4-phthalazinedione. 1,3,5-Cycloheptatriene (12.0 g., 0.13 ml.) is added to the cooled green solution (-50°) and white crystals precipitate almost immediately. After 10 minutes at -50°, the crude product (5.2 g.) is collected by filtration. Recrystallization of ~1/2 of the crude product (2.5 g.) from chloroform/acetone affords white granular crystals of 1,4-etheno-2,3-methano-1,2,3,4-tetrahydropyridazino[1,2-b]phthalazine-6,11-dione, mp 257°-259° C.

Provenance & Evidence