Tert-Butyl hypochlorite → 1,4-Phthalazinedione

Participants

Reaction Steps

To a solution of t-butyl hypochlorite (3.8 g., 0.038 m.) in acetone (200 ml.), cooled to -60° is added the sodium salt of phthalhydrazide (4.8 g., 0.021 m.). After 2.5 hours at -60° to -50°, the green reaction mixture is filtered to give a solution of 1,4-phthalazinedione. 1,3-Cyclohexadiene (2.0 ml.) is added to the cooled green solution (-50°) and white crystals precipitate almost immediately. After 10 minutes at -50°, the crude product (3.0 g.) is collected by filtration. Recrystallization from chloroform/acetone affords white microprisms of 1,4-ethano-1,4-dihydropyridazino[1,2-b]phthalazine-6,11-dione, mp >250° C.

Provenance & Evidence