Tert-Butyl hypochlorite → 1,4-Phthalazinedione

HRID 1413424Notes

Reaction equation

HRID 1413424 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°, is added the sodium salt of phthalhydrazide (4.8 g., 0.021 g.). After 2.5 hours at -60° to -50°, the resulting green reaction mixture is filtered to give a solution of 1,4-phthalazinedione. Cyclopentadiene (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 CH2Cl2 /Et2O affords white microprisms of 1,4-methano-1,4-dihydropyridazino[1,2-b]phthalazine-6,11-dione (1.8 g., 64%), mp 206°-212° C.

Workup

  1. filtrationthe resulting green reaction mixture is filtered

Sources & evidence

ORD record
ord-5f4624fcd69a4fbd8342a9583057a0a3
Source dataset
uspto-grants-1981_02
Patent number
US04250180

Reaction notes

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