Reaction #3968

Reaction equation

2-[2-methoxy-5-nitro-4-(4,4-dimethyl-7-nitro-2H,4H-isoquinolin-1,3-dione-2-yl)-phenyl]-5-methoxy-imidazo[4,5-b]pyridine

hydrazine hydrate

→

2-(2-Methoxy-4-amino-5-nitro-phenyl)-5-methoxy-imidazo[4,5-b]pyridine

Solvents

isopropanol

Conditions

Workup

1. 1
   Temperaturerefluxed for 1.75 hours
2. 2
   ConcentrationThe reaction mixture is concentrated by evaporation
3. 3
   Otherthe residue is triturated with 50 ml of ice water
4. 4
   Otherthe product precipitated
5. 5
   Otheris purified by chromatography on silica gel [eluant: methylene chloride/ethanol (100:0 to 100:2)]

Procedure

One half gram of 2-[2-methoxy-5-nitro-4-(4,4-dimethyl-7-nitro-2H,4H-isoquinolin-1,3-dione-2-yl)-phenyl]-5-methoxy-imidazo[4,5-b]pyridine is suspended in 10 ml of isopropanol, mixed with 0.5 ml of 80% hydrazine hydrate, and refluxed for 1.75 hours with stirring. The reaction mixture is concentrated by evaporation, the residue is triturated with 50 ml of ice water, and the product precipitated is purified by chromatography on silica gel [eluant: methylene chloride/ethanol (100:0 to 100:2)].

Source