Reaction #75476

Reaction equation

3-nitroaniline

Nitric acid

cyanamide

→

title compound

Yield 57.0%

N-(3-Nitro-phenyl)-guanidine nitrate

Yield 57.0%

Solvents

EtOH

Conditions

Workup

1. 1
   Temperaturewas cooled on an ice bath
2. 2
   Temperaturewas then refluxed under N2 for a further 22 h
3. 3
   OtherThe solvent was evaporated
4. 4
   WashThe dark brown solid was washed with EtOAc/EtOH and dried-under high vacuum overnight

Procedure

A mixture of 3-nitroaniline (50 mmol, 6.90 g) in EtOH (10 mL) was cooled on an ice bath. Nitric acid (69% aq. soln.; 3.6 mL) was added dropwise. To this mixture cyanamide (50% aq soln.; 5 mL) was added. The reaction mixture was stirred at r.t. for 10 min and was then refluxed under N2 for a further 22 h. The solvent was evaporated. The dark brown solid was washed with EtOAc/EtOH and dried-under high vacuum overnight to afford the title compound as a brown solid (6.90 g, 57%). 1H-NMR (300 MHz, DMSO-d6) δ7.66-7.75 (m, 2H, Ph-H), 8.09-8.14 (m, 2H, Ph-H).

Source