Tert-Butyl hypochlorite → 1,4-Phthalazinedione

HRID 1413426Notes

Reaction equation

HRID 1413426 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 (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.

Workup

  1. filtrationthe reaction mixture is filtered

Sources & evidence

ORD record
ord-6ba455f0127c4f9e80db72355fa6108a
Source dataset
uspto-grants-1981_02
Patent number
US04250180

Reaction notes

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