Water → 2-methyl-4-(4-isopropylphenyl)-1-(2H)-phthalazinone

HRID 54995Notes

Reaction equation

HRID 54995 reaction equation
[CH3:1][NH:2][NH2:3].[CH:4]([C:7]1[CH:23]=[CH:22][C:10]([C:11]([C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15](O)=[O:16])=O)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].O>C1(C)C=CC=CC=1>[CH3:1][N:2]1[N:3]=[C:11]([C:10]2[CH:9]=[CH:8][C:7]([CH:4]([CH3:5])[CH3:6])=[CH:23][CH:22]=2)[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15]1=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 3457982-(4-Isopropylbenzoyl)benzoic acid

Product 1

HCID 199571122-methyl-4-(4-isopropylphenyl)-1-(2H)-phthalazinoneYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl hydrazine (8.05 g, 0.175 mol) was added to a mixture of 2-(4-isopropylbenzoyl)benzoic acid (40.2 g, 0.15 mol) in toluene (350 mL) and the mixture was heated to reflux for 3 hours with the removal of water with a Dean Stark trap. The reaction mixture was hot filtered through celite, the filtrate was concentrated to 125 mL and the filtrate was diluted with hexane (100 mL) and cooled. A solid was collected by filtration to afford 27.97 g (67%) of 2-methyl-4-(4-isopropylphenyl)-1-(2H)-phthalazinone, m.p. 107°-107.5° C.

Workup

  1. temperaturethe mixture was heated
  2. filtrationThe reaction mixture was hot filtered through celite
  3. concentrationthe filtrate was concentrated to 125 mL
  4. additionthe filtrate was diluted with hexane (100 mL)
  5. temperaturecooled
  6. filtrationA solid was collected by filtration

Sources & evidence

ORD record
ord-d46f1f2c94fc44ec92b392a644c3a265
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

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