Hydrazine hydrate (1:1) → 4-(3-amino-4-methoxybenzyl)-2H-phthalazin-1-one

HRID 459780

Reaktionsgleichung

Reaktionsgleichung von HRID 459780
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=O)[O:7]1.O.[NH2:22][NH2:23]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:7])[NH:23][N:22]=1

Komponenten

3

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 686248893-(3-amino-4-methoxybenzylidene)-3H-isobenzofuran-1-one

Produkt 1

HCID 184443744-(3-amino-4-methoxybenzyl)-2H-phthalazin-1-oneAusbeute 81,8 %

Versuchsvorschrift

A stirred mixture of the above 3-(3-amino-4-methoxybenzylidene)-3H-isobenzofuran-1-one (1.336 g, 0.005 mol), industrial methylated spirit (20 ml) and hydrazine monohydrate (0.25 g, 0.005 mol) was heated under reflux for 1.5 hours then cooled to ambient temperature. The resulting solid was collected by filtration, washed with water (5 ml), and dried in vacuo to give 4-(3-amino-4-methoxybenzyl)-2H-phthalazin-1-one (1.15 g) as a beige solid, m.pt. 211.5–214.5° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 3.75 (s, 3H) (—OCH3), 4.15 (s, 2H) (ArCH2—), 4.75 (s, 2H) (—NH2) 6.5–6.6 (m, 2H) (2×ArH), 6.7–6.75 (m, 1H) (ArH) 7.8–8.0 (m, 3H)(3×ArH), 8.3 (d, 1H) (ArH), 12.65 (s, 1H) (CONH); m/z (M+H)+. 282, 100% purity.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water (5 ml)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-41ec6333bd8f4bd5a103718a919560a5
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196085B2

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