Tert-Butyl hypochlorite → 1,4-Phthalazinedione

HRID 1438874Notes

Reaction equation

HRID 1438874 reaction equation
ClOC(C)(C)C.[Na].[C:8]([NH:20][NH2:21])(=[O:19])[C:9]1[C:10](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:11](NN)=[O:12]>CC(C)=O>[C:8]1(=[O:19])[C:9]2[C:10](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:11](=[O:12])[N:21]=[N:20]1

Participants

5

Reactant 3

HCID 521297Tert-Butyl hypochloriteHCID 5360545SodiumHCID 11367556Phthalohydrazide

Product 1

HCID 2835931,4-Phthalazinedione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  1. filtrationthe green reaction mixture was filtered

Sources & evidence

ORD record
ord-8812a7408474417a905bca012a171166
Source dataset
uspto-grants-1977_11
Patent number
US04057547

Reaction notes

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