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

HRID 459780Notes

Reaction equation

HRID 459780 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 184443744-(3-amino-4-methoxybenzyl)-2H-phthalazin-1-oneYield 81.8%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-41ec6333bd8f4bd5a103718a919560a5
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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