Tert-Butyl hypochlorite → 1,4-Phthalazinedione

HRID 1413427Notes

Reaction equation

HRID 1413427 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 -50°, is added to sodium salt of phthalhydrazide (12.4 g., 0.067 m.). The reaction mixture is stirred vigorously for 3 hours at -50° and then filtered to give a solution of 1,4-phthalazinedione. 1,3-Cyclooctadiene (12.0 g., 0.11 m.) is added to the green solution (-50°) and the green solution is warmed to 0°. The solution is kept at 0° until the green color is discharged (1.5 hours). The crude product (5.6 g.) is collected by filtration. Recrystallization of the crude product from methylene chloride-methanol affords white microprisms of 1,4-butano-1,4-dihydropyridazino[1,2-b]phthalazine-6,11-dione (5.0 g., 53%) mp 206°-207° C.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-3c92f2684bc04661a2b3446b58b34b9e
Source dataset
uspto-grants-1981_02
Patent number
US04250180

Reaction notes

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