Reaction #46257

Reaction equation

2-(5-oxo-4,5-dihydro-[1,2,4]triazin-6-ylmethyl)-isoindole-1,3-dione

hydrazine

→

title compound

6-aminomethyl-4H-[1,2,4]triazin-5-one

Solvents

CH2Cl2 EtOH

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated in vacuo
2. 2
   Otherthe off-white solid was triturated with warm CHCl3
3. 3
   Filtrationfiltered through a fritted funnel
4. 4
   OtherThe solid was then triturated with hot methanol (MeOH)
5. 5
   Filtrationfiltered through a fritted funnel
6. 6
   Otherresulting in an off-white solid
7. 7
   OtherThe material was triturated a second time as before and
8. 8
   Otherdried overnight

Procedure

A slurry of 2-(5-oxo-4,5-dihydro-[1,2,4]triazin-6-ylmethyl)-isoindole-1,3-dione (4 g, 15.6 mmol) in CH2Cl2/EtOH (1:1) (150 mL ) was charged with anhydrous hydrazine (1.23 mL, 39.0 mmol) and stirred at rt for 18 h. The reaction mixture was concentrated in vacuo and the off-white solid was triturated with warm CHCl3 and filtered through a fritted funnel. The solid was then triturated with hot methanol (MeOH) and filtered through a fritted funnel resulting in an off-white solid. The material was triturated a second time as before and dried overnight resulting in the title compound as a white solid, which was taken on to the next step without further purification; 1H NMR (DMSO-d6, 400 MHz) δ 3.88(s, 2H), 8.31 (2, 1H); MS (ES+): m/z 127.07 (100) [MH+], HPLC: tR=0.34 min (MicromassZQ, polar—5 min).

Source