P-Phenylenediamine → N-[3-(4-Methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-benzene-1,4-diamine

HRID 424405Notes

Reaction equation

HRID 424405 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2=[N:12][N:13]=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:4]2[N:3]=1.[C:23]1([NH2:30])[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>C(O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[N:4]3[N:3]=[C:2]([NH:29][C:26]4[CH:27]=[CH:28][C:23]([NH2:30])=[CH:24][CH:25]=4)[C:11]4[C:6]([C:5]3=[N:12][N:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 7126896-Chloro-3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazine2×

Product 1

HCID 66703856N-[3-(4-Methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-benzene-1,4-diamineYield 84.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g 6-chloro-3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazine (compound B1) and 2.7 g p-phenylene-diamine are stirred at 170° C. for 5 h. The reaction mixture is diluted with 6 ml ethanol and the precipitate is filtered with suction. The solid is recrystallized from N,N-dimethylformamide to yield 1.04 g of the title compound (m.p.: 295° C.).

Workup

  1. filtrationthe precipitate is filtered with suction
  2. customThe solid is recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-393a97d1a4d84efe86203b9ffd398b93
Source dataset
uspto-grants-2012_01
Patent number
US08106047B2

Reaction notes

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