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) which was cooled to -60°, was added the sodium salt of phthalhydrazide (4.8 g, 0.021 m). After 2.5 hours at -60° to -50°, the green reaction mixture was filtered to give a clear green solution of 1,4-phthalazinedione. 1-Methyl-2-pyridone (2.0 g, 1.8 eq., based on reacted phthalhyrazide) was added to the green solution and the resulting solution was kept at -60° for 40 minutes, allowed to warm up to 0°, and then kept at 0° for another hour. The light green solution was concentrated under reduced pressure to a volume of 10 ml. Addition of ether (30 ml) precipitated the crude product which was collected by filtration (1.8g).

Provenance & Evidence