Reaction #1483054

Reaction equation

tetrachloro-1,4-benzoquinone

4-Aminobenzamidine dihydrochloride

formamidine acetate

hydrazine

→

4-(1,2,4,5-tetrazin-3-yl)aniline

Yield 19.1%

Solvents

acetonitrile

Conditions

Workup

1. 1
   TemperatureThe solution was heated
2. 2
   Temperatureto reflux for 1 hour
3. 3
   Temperaturecooled
4. 4
   Otherthe solvent was removed by rotary evaporation
5. 5
   OtherAfter removal of the solids from the pink solution
6. 6
   Filtrationby filtration
7. 7
   Concentrationthe reaction was concentrated by rotary evaporation
8. 8
   Otherpurified by preparative HPLC

Procedure

To a mixture of 4-Aminobenzamidine dihydrochloride (1 mmol, 208 mg) and formamidine acetate (4 mmol, 416 mg) in acetonitrile (25 mL) was added anhydrous hydrazine (10 mmol, 315 uL). The solution was heated to reflux for 1 hour, cooled, and the solvent was removed by rotary evaporation. The residue was resuspended with water (25 mL) and was stirred with solid tetrachloro-1,4-benzoquinone (2 mmol, 492 mg) for 1 hour. After removal of the solids from the pink solution by filtration, the reaction was concentrated by rotary evaporation and purified by preparative HPLC using a gradient from 0-40% buffer B (buffer A is water with 0.1% TFA, and buffer B is acetonitrile with 10% water and 0.1% TFA) to afford pure 4-(1,2,4,5-tetrazin-3-yl)aniline (33 mg, 19%), as a pink solid. LRMS-ESI [M+H]+ calcd. for C8H8N5+: 174.08, found: 173.9.

Source