3,4-Dicyanophenol

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.52 g portion of 4-hydroxyphthalonitrile was dissolved in 30.0 ml of acetonitrile, mixed with 2.1 ml of triethylamine and stirred at −10° C. The reaction solution was mixed with 1.8 ml of anhydrous trifluoromethanesulfonic acid, stirred at 0° C. for 30 minutes and then warmed up to room temperature, mixed with 15 ml of DMF and stirred for 2 hours. After evaporation of the solvent under reduced pressure, the residue was mixed with ethyl acetate and washed with saturated aqueous sodium bicarbonate and then the organic layer was dried over sodium sulfate. After evaporation of the solvent under reduced pressure, the residue was dissolved in 20 ml of acetonitrile and mixed with 2.30 g of 2,5-transmethylpiperazine, and the mixture was heated under reflux for 2 hours and then stirred overnight at room temperature. After evaporation of the solvent under reduced pressure, the residue was mixed with 100 ml of ethyl acetate, washed with saturated aqueous sodium bicarbonate and saturated brine and then dried over sodium sulfate. The title compound was obtained by evaporating the solvent under reduced pressure. stirred at 0° C. for 30 minutes warmed up to room temperature stirred for 2 hours After evaporation of the solvent under reduced pressure the residue was mixed with ethyl acetate washed with saturated aqueous sodium bicarbonate the organic layer was dried over sodium sulfate After evaporation of the solvent under reduced pressure the residue was dissolved in 20 ml of acetonitrile mixed with 2.30 g of 2,5-transmethylpiperazine the mixture was heated under reflux for 2 hours stirred overnight at room temperature After evaporation of the solvent under reduced pressure the residue was mixed with 100 ml of ethyl acetate washed with saturated aqueous sodium bicarbonate and saturated brine dried over sodium sulfate

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

Procedure: A stirred suspension of 4-hydroxyphthalonitrile (3.5 g; 24.3 mmol), K2CO3 (4.03 g; 29.2 mmol) and 2-{[(3-nitrophenyl)sulfonyloxy]methyl}-oxirane (6.50 g; 25.0 mmol; see Example B above) in MeCN (170 mL) was refluxed for 1.5 h. The cooled reaction mixture was filtered, the filtrate concentrated and the solid residue recrystallized from IPA to give the sub-title compound. was refluxed for 1.5 h The cooled reaction mixture was filtered the filtrate concentrated the solid residue recrystallized from IPA

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

Procedure: In 200 ml of N,N-dimethylformamide were dissolved with heating 20 g of 4-hydroxyphthalonitrile and 10.55 g of potassium carbonate, to which 20 g of chloroethyl-trimethylsilane were added dropwise at 40° C. in the atmosphere of argon. Immediately after the addition, the mixture was stirred for 18 hours while maintaining the reaction temperature at 85°-105° C. The reaction vessel was then cooled to room temperature and 250 ml of dilute hydrochloric acid was added. The mixture was extracted with 1.2 liters of toluene. The organic layer was washed well with water and water was removed with magnesium sulfate. Thereafter, toluene was removed by distillation and the residue was purified with a toluene/silica gel column to obtain 24.6 g (yield: 77.0%) of a compound having the formula (XVII) below. ##STR39## Immediately after the addition while maintaining the reaction temperature at 85°-105° C The mixture was extracted with 1.2 liters of toluene The organic layer was washed well with water and water was removed with magnesium sulfate Thereafter, toluene was removed by distillation the residue was purified with a toluene/silica gel column