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

HRID 1769151

Reaktionsgleichung

Reaktionsgleichung von HRID 1769151
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 199570362-methyl-4-(2,4-diethylphenyl)-1-(2H)-phthalazinoneAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c30346a56576463495d0501209ac7df9
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380721

Verknüpfte Notizen

Wird geladen…