p-Anisoyl chloride → 6-Chloro-3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazine

HRID 2241862Notes

Reaction equation

HRID 2241862 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][NH2:13])=[N:4][N:3]=1.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[Cl:1][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:20]([C:19]3[CH:23]=[CH:24][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)[N:4]2[N:3]=1

Participants

5

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 27937521-Chloro-4-hydrazinophthalazine2×

Product 1

HCID 7126896-Chloro-3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazineYield 54.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
110 °C

Procedure

6.0 g (4-chloro-phthalazin-1-yl)-hydrazine (compound C1) are suspended in a mixture of 160 ml toluene and 18 ml triethylamine at 60° C. and treated with a solution of 6.0 g 4-methoxy-benzoyl chloride in 48 ml toluene. The mixture is stirred at 110° C. for 6 h, cooled to ambient temperature, filtered with suction and rinsed with toluene. The solid is recrystallized from N,N-dimethylformamide, the precipitate is washed with water and dried to yield 5.2 g of the title compound (m.p.: 192-193° C.).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered with suction
  3. washrinsed with toluene
  4. customThe solid is recrystallized from N,N-dimethylformamide
  5. washthe precipitate is washed with water
  6. customdried

Sources & evidence

ORD record
ord-754c7b93dbbc4c6cbc822f5b8eff86d3
Source dataset
uspto-grants-2010_03
Patent number
US07671050B2

Reaction notes

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