Reaction #75482

Reaction equation

4-amino-2-nitrophenol

nitric acid

cyanamide

→

title compound

Yield 54.0%

N-(4-Hydroxy-2-nitro-phenyl)-guanidine nitrate

Yield 54.0%

Solvents

EtOH

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed under N2 for 22 h
2. 2
   OtherThe solvent was evaporated
3. 3
   WashThe dark brown solid residue was washed with EtOH
4. 4
   Otherwas dried under high vacuum

Procedure

A mixture of 4-amino-2-nitrophenol (25 mmol, 3.85 g) in EtOH (6 mL) on an ice bath was treated with nitric acid (69% aq soln.; 1.8 mL). To this of cyanamide (50% aq. soln.; 4 mL) was added. The reaction mixture was refluxed under N2 for 22 h. The solvent was evaporated. The dark brown solid residue was washed with EtOH and was dried under high vacuum to afford the title compound as a grey solid (3.53 g, 54%).

Source