Reaction #2329045

ord-9cfa7a6e1fbe438099b3860e2ab55a88

Reaction equation

O=C(Cl)c1ccccc1
benzoic acid chloride
NNc1nnc(Cl)c2ccccc12
(4-chloro-phthalazin-1-yl)-hydrazine
NNc1nnc(Cl)c2ccccc12
compound C1
NNc1nnc(Cl)c2ccccc12
(4-chloro-phthalazin-1-yl)-hydrazine
O=C(NN=c1[nH]nc(Cl)c2ccccc12)c1ccccc1
benzoic acid (4-chloro-2H-phthalazin-1-ylidene)-hydrazide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureat reflux temperature
  2. 2
    Filtrationfiltered with suction
  3. 3
    ConcentrationThe filtrate is concentrated under reduced pressure
  4. 4
    Otherthe residue is recrystallized from N,N-dimethylformamide

Procedure

2.5 g (4-chloro-phthalazin-1-yl)-hydrazine (compound C1) are suspended in 250 ml toluene and treated with a solution of 1.7 ml benzoic acid chloride in 50 ml toluene at reflux temperature. After 2 h the reaction mixture is cooled to ambient temperature and filtered with suction. The filtrate is concentrated under reduced pressure and the residue is recrystallized from N,N-dimethylformamide to yield 1.2 g of benzoic acid (4-chloro-2H-phthalazin-1-ylidene)-hydrazide.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07671050B2uspto-grants-2010_03