1-phenylpentane-1,4-dione

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

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

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

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

Procedure: Following the description in Example 1, 5.1 g (approx. 0.02 mol) of Cat. 3, 21.2 g (0.2 mol) of distilled benzaldehyde, 350 ml of dimethylformamide and 14 g (0.2 mol) of stabilized methyl vinyl ketone are introduced into a 500 ml three-necked flask. After displacing the air by pure nitrogen, the mixture is brought to a temperature of 80° C and 14.9 g (0.1 mol) of triethanolamine are added. The mixture is then stirred for 15 hours at the same temperature. Working up takes place as in Example 11 except that the mixture is filtered after having been taken up in chloroform. 1-Phenyl-pentane-1,4-dione is obtained. are added is filtered

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

Procedure: Following the description in Example 1, 5.1 g (approx. 0.02 mol) of Cat. 3, 21.2 g (0.2 mol) of distilled benzaldehyde, 350 ml of dimethylformamide and 14 g (0.2 mol) of stabilized methyl vinyl ketone are introduced into a 500 ml three-necked flask. After displacing the air by pure nitrogen, the mixture is brought to a temperature of 80° C and 14.9 g (0.1 mol) of triethanolamine are added. The mixture is then stirred for 15 hours at the same temperature. Working up takes place as in Example 11 except that the mixture is filtered after having been taken up in chloroform. 1-Phenyl-pentane-1,4-dione is obtained. are added is filtered

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

Procedure: To a well stirred suspension of anhydrous aluminium chloride (27.0 g, 205.9 mmol) in 126 ml of benzene was added 4-oxopentanoylchloride (23.0 g, 171.6 mmol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and the filtrate evaporated on a rotary evaporator to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml) and dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform as eluent to give 8.6 g (24.07%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered the filtrate evaporated on a rotary evaporator to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

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

Procedure: 25 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 10 ml of toluene. To the mixture were added 20 mg of 1-phenyl-1,4-pentandione and 0.2 mg of p-toluenesulfonate (hydrate), followed by heating under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12 mg of the title compound. by heating under reflux for 1 hour by extracting with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate The solvent was evaporated the residue was purified by silica gel chromatography (hexane/ethyl acetate system)

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

Procedure: 25 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 10 ml of toluene. To the mixture were added 20 mg of 1-phenyl-1,4-pentandione and 0.2 mg of p-toluenesulfonate (hydrate), followed by heating under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12 mg of the title compound. by heating under reflux for 1 hour by extracting with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate The solvent was evaporated the residue was purified by silica gel chromatography (hexane/ethyl acetate system)

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

Procedure: 25 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 10 ml of toluene. To the mixture were added 20 mg of 1-phenyl-1,4-pentandione and 0.2 mg of p-toluenesulfonate (hydrate), followed by heating under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12 mg of the title compound. by heating under reflux for 1 hour by extracting with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate The solvent was evaporated the residue was purified by silica gel chromatography (hexane/ethyl acetate system)

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

Procedure: Following the description in Example 1, 5.1 g (approx. 0.02 mol) of Cat. 3, 21.2 g (0.2 mol) of distilled benzaldehyde, 350 ml of dimethylformamide and 14 g (0.2 mol) of stabilized methyl vinyl ketone are introduced into a 500 ml three-necked flask. After displacing the air by pure nitrogen, the mixture is brought to a temperature of 80° C and 14.9 g (0.1 mol) of triethanolamine are added. The mixture is then stirred for 15 hours at the same temperature. Working up takes place as in Example 11 except that the mixture is filtered after having been taken up in chloroform. 1-Phenyl-pentane-1,4-dione is obtained. are added is filtered

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

Procedure: 25 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 10 ml of toluene. To the mixture were added 20 mg of 1-phenyl-1,4-pentandione and 0.2 mg of p-toluenesulfonate (hydrate), followed by heating under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12 mg of the title compound. by heating under reflux for 1 hour by extracting with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate The solvent was evaporated the residue was purified by silica gel chromatography (hexane/ethyl acetate system)

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

Procedure: 25 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 10 ml of toluene. To the mixture were added 20 mg of 1-phenyl-1,4-pentandione and 0.2 mg of p-toluenesulfonate (hydrate), followed by heating under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12 mg of the title compound. by heating under reflux for 1 hour by extracting with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate The solvent was evaporated the residue was purified by silica gel chromatography (hexane/ethyl acetate system)