N',4-dihydroxybenzenecarboximidamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a dimethylsulfoxide (100 mL) solution of 10.0 g of 4-cyanophenol was dropwise added 12.9 mL of a 50% hydroxylamine aqueous solution at room temperature over a period of 6 minutes, which was then stirred at the same temperature for 14 hours. Chloroform, a 1 mol/L sodium hydroxide aqueous solution, and water were added to the reaction mixture. The aqueous layer was separated and washed sequentially with toluene, chloroform, and toluene, to which water was then added, followed by adjustment to pH 7.2 using 6 mol/L hydrochloric acid. After stirring this mixture at room temperature for 30 minutes, the precipitate was collected by filtration and washed with water to provide 8.88 g of N′, 4-dihydroxybenzamidine as white solid form. at room temperature of 6 minutes The aqueous layer was separated washed sequentially with toluene, chloroform, and toluene, to which water was then added After stirring this mixture at room temperature for 30 minutes the precipitate was collected by filtration washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N′,4-Dihydroxybenzenecarboximidamide (1.28 g, 8.4 mmol) was suspended in 3 mL ethanol and 3 mL trimethylorthoformate in a 20 mL biotage microwave reaction tube. The mixture was sealed and microwaved at 150° C. for 10 min. The solvent was removed by concentration and the residue was purified by column chromatography eluting with 20% DCM/hexanes to give the desired product as white solid. LRMS calc: 162.0; obs: 163.2 (M+1). The mixture was sealed microwaved at 150° C. for 10 min The solvent was removed by concentration the residue was purified by column chromatography eluting with 20% DCM/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a dimethylsulfoxide (100 mL) solution of 10.0 g of 4-cyanophenol was dropwise added 12.9 mL of a 50% hydroxylamine aqueous solution at room temperature over a period of 6 minutes, which was then stirred at the same temperature for 14 hours. Chloroform, a 1 mol/L sodium hydroxide aqueous solution, and water were added to the reaction mixture. The aqueous layer was separated and washed sequentially with toluene, chloroform, and toluene, to which water was then added, followed by adjustment to pH 7.2 using 6 mol/L hydrochloric acid. After stirring this mixture at room temperature for 30 minutes, the precipitate was collected by filtration and washed with water to provide 8.88 g of N′, 4-dihydroxybenzamidine as white solid form. at room temperature of 6 minutes The aqueous layer was separated washed sequentially with toluene, chloroform, and toluene, to which water was then added After stirring this mixture at room temperature for 30 minutes the precipitate was collected by filtration washed with water