Phthalic Anhydride → 2,3-Dihydro-1,4-phthalazinedione

HRID 1176187Notes

Reaction equation

HRID 1176187 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.O.[NH2:13][NH2:14]>C(O)(=O)C>[C:4]1(=[O:5])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:6])[NH:14][NH:13]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 2194012,3-Dihydro-1,4-phthalazinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compounds of this invention with Formulae I-VIII could be prepared as illustrated by the exemplary reaction in Scheme 20. Reaction of phthalic anhydride with hydrazine hydrate in acetic acid produces 2,3-dihydro-phthalazine-1,4-dione. Chlorination of 2,3-dihydro-phthalazine-1,4-dione and subsequent reaction with an amine, such as N-methyl-p-anisidine, produces the substituted 4-chlorophthalazine, such as (4-chlorophthalazin-1-yl)(4-methoxyphenyl)-amine. The chloro group can then be removed via hydrogenation to produce the substituted phthalazine, such as (4-methoxyphenyl)-methylphthalazin-1-yl-amine.

Workup

  1. customCompounds of this invention with Formulae I-VIII could be prepared
  2. customas illustrated by the exemplary reaction in Scheme 20

Sources & evidence

ORD record
ord-d862c4a3bfe1490db6bb8cdf95ef149e
Source dataset
uspto-grants-2010_11
Patent number
US07842805B2

Reaction notes

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