Water → 4-(3,4-Dichlorophenyl)-2-methylphthalazin-1(2H)-one

HRID 54998Notes

Reaction equation

HRID 54998 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10])=O.[CH3:20][NH:21][NH2:22].O>C1(C)C=CC=CC=1>[CH3:20][N:21]1[N:22]=[C:5]([C:4]2[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Cl:1])[CH:3]=2)[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 7933562-(3,4-Dichlorobenzoyl)benzoic acid

Product 1

HCID 142443714-(3,4-Dichlorophenyl)-2-methylphthalazin-1(2H)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(3,4-dichlorobenzoyl)benzoic acid (29.4 g, 0.1 mol) in toluene (100 mL) was added methyl hydrazine (5.8 mL). The mixture was brought to reflux for 3 hours, with the removal of water via a Dean Stark trap. The mixture was cooled, and the product was collected by filtration to afford 25.54 g (84%) of 2-Methyl-4-(3,4-dichlorophenyl)-1-(2H)-phthalazinone, m.p. 179°-181° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-d90194ca2c0d4a129e6fb6d50732faf6
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

Loading…