Toluene → 2-methyl-4-(3-chloro-4-methoxyphenyl)-1-(2H)-phthalazinone

HRID 55001Notes

Reaction equation

HRID 55001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10])=O.C1(C)C=CC=CC=1.[CH3:28][NH:29][NH2:30]>O>[CH3:28][N:29]1[N:30]=[C:5]([C:4]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[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 1140TolueneHCID 6061MethylhydrazineHCID 199571722-(3-Chloro-4-methoxybenzoyl)benzoic acid

Product 1

HCID 199570632-methyl-4-(3-chloro-4-methoxyphenyl)-1-(2H)-phthalazinoneYield 68.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(3-chloro-4-methoxybenzoyl)benzoic acid (10.46 g, 0.036 mol), toluene (50 mL) and methyl hydrazine (2.1 mL) was refluxed in the presence of a Dean Stark trap until the theoretical amount of water had been collected. The reaction mixture was cooled, and the product was collected by filtration to afford 7.42 g (68.7%) of 2-methyl-4-(3-chloro-4-methoxyphenyl)-1-(2H)-phthalazinone, m.p. 195°-195° C. An additional 1.89 g of product was also collected from the filtrate for a total of 9.31 g (86.2%).

Workup

  1. customhad been collected
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-43be2c63af9d4ce2a1fec719f1f509cb
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

Loading…