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

HRID 459747Notes

Reaction equation

HRID 459747 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=O)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.[NH2:22][NH2:23]>>[NH2:1][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18](=[O:19])[NH:23][N:22]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 123282872-(3-Nitrophenyl)-1H-indene-1,3(2H)-dione

Product 1

HCID 184443754-(3-aminobenzyl)-2H-phthalazin-1-one

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 2-(3-nitrophenyl)indan-1,3-dione (85 g, 0.318 mol) and hydrazine hydrate (450 ml) was heated under reflux for 2 hours then cooled to 0° C. The resulting solid was collected by filtration, washed with water (500 ml), ground to a fine powder, mixed with sufficient cold ethanol to give a thick paste, collected by filtration and dried in vacuo at 55° C. The crude solid was then recrystallised from ethanol to give 4-(3-aminobenzyl)-2H-phthalazin-1-one (32.6 g) as a pale brown solid, m.pt. 175–177° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water (500 ml), ground to a fine powder
  5. additionmixed with sufficient cold ethanol
  6. customto give a thick paste
  7. filtrationcollected by filtration
  8. customdried in vacuo at 55° C
  9. customThe crude solid was then recrystallised from ethanol

Sources & evidence

ORD record
ord-74c0e87339e44325a331ba236c0b536a
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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