(2-bromophenyl)hydrazine

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 1,2-Diphenylethane-1,2-dione (2-bromophenyl)hydrazone was prepared from 2-bromophenyl hydrazine and 1,2-diphenyl-ethane-1,2-dione according to the procedure of Step 1 Example 2. MS m/z 379;

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 15 g 2-bromophenylhydrazine hydrochloride are suspended in 400 ml of toluene and combined with 240 ml of 1 N sodium hydroxide solution. The mixture is stirred for 1 hour and the phases are separated. The organic phase is dried on magnesium sulphate and the solvents are eliminated in vacuo. The crude product thus obtained is further reacted directly. the phases are separated The organic phase is dried on magnesium sulphate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11.0 g 2-bromophenylhydrazine and 550 mg p-toluenesulphonic acid monohydrate are dissolved in 200 ml of toluene, combined with 6.74 ml ethyl pyruvate and refluxed for 2 hours using the water separator. The mixture is allowed to cool to 40° C. and combined with a solution that is obtained by dissolving 44.75 g p-toluenesulphonic acid monohydrate in 300 ml of toluene and refluxing for two hours using the water separator. Then the mixture is refluxed for 12 hours using the water separator. After cooling to ambient temperature the solvents are eliminated in vacuo, the residue is taken up in ethyl acetate and washed successively with water and saturated aqueous sodium hydrogen carbonate solution. After drying with magnesium sulphate the mixture is combined with activated charcoal, stirred for 15 minutes and filtered through kieselguhr. The process of adding activated charcoal, stirring and filtering is repeated twice more. The solvents are eliminated in vacuo and the residue is taken up in petroleum ether/dichloromethane 7:3. 30 g of silica gel are added, the mixture is stirred for 10 minutes and then suction filtered through kieselguhr. The suction filtered silica gel is washed with petroleum ether/dichloromethane 7:3. The solvents are eliminated in vacuo. refluxed for 2 hours is obtained refluxing for two hours Then the mixture is refluxed for 12 hours After cooling to ambient temperature the solvents washed successively with water and saturated aqueous sodium hydrogen carbonate solution After drying with magnesium sulphate the mixture filtered through kieselguhr The process of adding activated charcoal stirring filtering 30 g of silica gel are added the mixture is stirred for 10 minutes suction filtered through kieselguhr The suction filtered silica gel is washed with petroleum ether/dichloromethane 7:3

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11.0 g 2-bromophenylhydrazine and 550 mg p-toluenesulphonic acid monohydrate are dissolved in 200 ml of toluene, combined with 6.74 ml ethyl pyruvate and refluxed for 2 hours using the water separator. The mixture is allowed to cool to 40° C. and combined with a solution that is obtained by dissolving 44.75 g p-toluenesulphonic acid monohydrate in 300 ml of toluene and refluxing for two hours using the water separator. Then the mixture is refluxed for 12 hours using the water separator. After cooling to ambient temperature the solvents are eliminated in vacuo, the residue is taken up in ethyl acetate and washed successively with water and saturated aqueous sodium hydrogen carbonate solution. After drying with magnesium sulphate the mixture is combined with activated charcoal, stirred for 15 minutes and filtered through kieselguhr. The process of adding activated charcoal, stirring and filtering is repeated twice more. The solvents are eliminated in vacuo and the residue is taken up in petroleum ether/dichloromethane 7:3. 30 g of silica gel are added, the mixture is stirred for 10 minutes and then suction filtered through kieselguhr. The suction filtered silica gel is washed with petroleum ether/dichloromethane 7:3. The solvents are eliminated in vacuo. refluxed for 2 hours is obtained refluxing for two hours Then the mixture is refluxed for 12 hours After cooling to ambient temperature the solvents washed successively with water and saturated aqueous sodium hydrogen carbonate solution After drying with magnesium sulphate the mixture filtered through kieselguhr The process of adding activated charcoal stirring filtering 30 g of silica gel are added the mixture is stirred for 10 minutes suction filtered through kieselguhr The suction filtered silica gel is washed with petroleum ether/dichloromethane 7:3

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11.0 g 2-bromophenylhydrazine and 550 mg p-toluenesulphonic acid monohydrate are dissolved in 200 ml of toluene, combined with 6.74 ml ethyl pyruvate and refluxed for 2 hours using the water separator. The mixture is allowed to cool to 40° C. and combined with a solution that is obtained by dissolving 44.75 g p-toluenesulphonic acid monohydrate in 300 ml of toluene and refluxing for two hours using the water separator. Then the mixture is refluxed for 12 hours using the water separator. After cooling to ambient temperature the solvents are eliminated in vacuo, the residue is taken up in ethyl acetate and washed successively with water and saturated aqueous sodium hydrogen carbonate solution. After drying with magnesium sulphate the mixture is combined with activated charcoal, stirred for 15 minutes and filtered through kieselguhr. The process of adding activated charcoal, stirring and filtering is repeated twice more. The solvents are eliminated in vacuo and the residue is taken up in petroleum ether/dichloromethane 7:3. 30 g of silica gel are added, the mixture is stirred for 10 minutes and then suction filtered through kieselguhr. The suction filtered silica gel is washed with petroleum ether/dichloromethane 7:3. The solvents are eliminated in vacuo. refluxed for 2 hours is obtained refluxing for two hours Then the mixture is refluxed for 12 hours After cooling to ambient temperature the solvents washed successively with water and saturated aqueous sodium hydrogen carbonate solution After drying with magnesium sulphate the mixture filtered through kieselguhr The process of adding activated charcoal stirring filtering 30 g of silica gel are added the mixture is stirred for 10 minutes suction filtered through kieselguhr The suction filtered silica gel is washed with petroleum ether/dichloromethane 7:3

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

Procedure: The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and (2-bromo-phenyl)-hydrazine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO at 60° C.) δ 9.19 (br, 1H), 7.66 (brd, 1H), 7.46 (d, 1H), 7.44 (br, 1H), 7.20 (t, 1H), 6.98-6.75 (3H), 6.71 (t, 1H), 6.23 (s, 1H), 3.94 (t, 2H), 3.82 (s, 3H) and 2.93 (t, 2H); MS (ESI) (M+H)+ 413, 415.

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

Procedure: The acetaldehyde 1-benzoyl-1-(2-bromophenyl) hydrazone was prepared as follows: A solution of 11.2 g. of 2-bromophenyl hydrazine in ether was treated with 7 ml. of acetaldehyde and allowed to stand for 1 hour with occasional swirling. The ether solution was washed with water, a small amount of dilute potassium bicarbonate solution, and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was taken up in 25 ml. dry dimethylformamide and the resulting solution was added dropwise, with stirring and water-bath cooling, to a mixture of 1.56 g. of sodium hydride in 25 ml. dry dimethylformamide and stirring was continued for 1 hour. To this solution under nitrogen was added dropwise with stirring a solution of 7 ml. of benzoyl chloride in 10 ml. of dimethylformamide and stirring was continued for 4 hours. The mixture was diluted with ether and treated with water containing sufficient glacial acetic acid to neutralize excess alkali. The ether extract was washed with water, dilute potassium carbonate solution, water, and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give acetaldehyde 1-benzoyl-1-(2-bromophenyl) hydrazone which was used as such in the above reaction. The acetaldehyde 1-benzoyl-1-(2-bromophenyl) hydrazone was prepared The ether solution was washed with water a small amount of dilute potassium bicarbonate solution, and saturated sodium chloride solution, dried over magnesium sulfate evaporated to dryness under reduced pressure dry dimethylformamide and the resulting solution was added dropwise water-bath cooling, to a mixture of 1.56 g dry dimethylformamide and stirring was continued for 1 hour To this solution under nitrogen was added dropwise with stirring a solution of 7 ml of dimethylformamide and stirring was continued for 4 hours The mixture was diluted with ether treated with water containing sufficient glacial acetic acid The ether extract was washed with water, dilute potassium carbonate solution, water, and saturated sodium chloride solution dried over magnesium sulfate evaporated to dryness under reduced pressure

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

Procedure: 1,2-Diphenylethane-1,2-dione (2-bromophenyl)hydrazone was prepared from 2-bromophenyl hydrazine and 1,2-diphenyl-ethane-1,2-dione according to the procedure of Step 1 Example 2. MS m/z 379;