2-bromo-N-(2,6-dimethylphenyl)butanamide

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: A mixture of 7.7 g (28.5 mmoles) of N-(2-bromo-butyryl)-2,6-dimethyl-aniline, 70 ml of ethanol and 20 ml of a 33% aqueous dimethyl amine solution is heated in a bomb at 100°-110° C. for 6 hours. The mixture is cooled, diluted with 150 ml of diethyl ether and 40 ml of water, the phases are separated, and the aqueous phase is extracted twice with 25 ml of diethyl ether, each. The etheral solutions are combined, washed thrice with 35 ml of 1 n aqueous hydrochloric acid, each, the aqueous acidic solutions are combined, rendered alkaline (pH=9) with concentrated aqueous ammonia, and extracted thrice with 40 ml of 1,2-dichloroethane, each. The dichloroethane solutions are combined, washed thrice with 20 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The oily residue, weighing 7.1 g, is triturated with diisopropyl ether to obtain 4.1 g of crude product, which is recrystallized then from ethyl acetate. 3.2 g (47.9%) of pure N-(2-dimethylamino-butyryl)-2,6-dimethyl-aniline are obtained; m.p.: 155°-157° C. is heated in a bomb at 100°-110° C. for 6 hours The mixture is cooled the phases are separated the aqueous phase is extracted twice with 25 ml of diethyl ether washed thrice with 35 ml of 1 n aqueous hydrochloric acid extracted thrice with 40 ml of 1,2-dichloroethane washed thrice with 20 ml of water each, dried over anhydrous magnesium sulfate the solvent is evaporated under reduced pressure is triturated with diisopropyl ether to obtain 4.1 g of crude product, which is recrystallized

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 20.0 g (74 mmoles) of N-(2-bromo-butyryl)--2,6-dimethyl-aniline, 27.8 g (0.15 moles) of potassium phthalimide and 150 ml of dry dimethyl formamide is stirred at 60° C. for 2 hours. The mixture is cooled, poured onto 750 ml of ice water, the separated crystalline substance is filtered off, washed with water and dried. The resulting crude product, weighing 35.7 g, is dissolved in 200 ml of chloroform, the solution is washed thrice with 50 ml of 1 n aqueous sodium hydroxide solution and thrice with 50 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. 17.7 g (71.1%) of N-(2-phthalimido-butyryl)-2,6-dimethyl-aniline are obtained; m.p.: 195°-196° C. The mixture is cooled the separated crystalline substance is filtered off washed with water dried is dissolved in 200 ml of chloroform the solution is washed thrice with 50 ml of 1 n aqueous sodium hydroxide solution and thrice with 50 ml of water each, dried over anhydrous magnesium sulfate the solvent is evaporated under reduced pressure

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