Toluene → 2-methyl-4-(2,4-diethylphenyl)-1-(2H)-phthalazinone

HRID 55003

Reaction equation

HRID 55003 reaction equation
[CH2:1]([C:3]1[CH:19]=[C:18]([CH2:20][CH3:21])[CH:17]=[CH:16][C:4]=1[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10])=O)[CH3:2].C1(C)C=CC=CC=1.[CH3:29][NH:30][NH2:31]>O>[CH3:29][N:30]1[N:31]=[C:5]([C:4]2[CH:16]=[CH:17][C:18]([CH2:20][CH3:21])=[CH:19][C:3]=2[CH2:1][CH3:2])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:10]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 6061Methylhydrazine2×HCID 199571532-(2,4-Diethylbenzoyl)benzoic acid

Product 1

HCID 199570362-methyl-4-(2,4-diethylphenyl)-1-(2H)-phthalazinoneYield 55.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-(2,4-diethylbenzoyl)benzoic acid (40 g, 0.14 mol), toluene (120 mL) and methyl hydrazine (7.5 mL) were refluxed for 3 hours with removal of water via a Dean Stark trap. Additional toluene (100 mL) and methyl hydrazine (4.0 mL) were added and the mixture was refluxed until 2.8 mL of water was collected. The mixture was cooled, extracted with CH2Cl2 /2N NaOH, then 1N HCl and the organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was crystallized from ethanol/water and recrystallized from ethanol/water to afford 22.86 g (55.9%) of 2-methyl-4-(2,4-diethylphenyl)-1-(2H)-phthalazinone, m.p. 94.5°-96.5° C.

Workup

  1. customwas collected
  2. temperatureThe mixture was cooled
  3. extractionextracted with CH2Cl2 /2N NaOH
  4. custom1N HCl and the organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from ethanol/water
  8. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-aca86f0e6b0b44d39dbfaba43b7fdc67
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Linked notes

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