Formaldehyde → 3-(Dimethylamino)-2-methyl-1-(3-nitro-phenyl)-propan-1-one

Participants

Reaction Conditions

Reaction Steps

N,N-dimethylamine HCl (80.0 g, 0.982 mol), paraformaldehyde (45 g, 1.499 mol), water (30 g, 1.667 mol) and acetic anhydride (30 ml/32.4 g, 0.32 mol) are added into a 1 liter four-neck flask, provided with mechanical stirrer, thermometer and dropping funnel. The suspension is slowly heated up to 50° C. and stirred for 30 minutes. Then, acetic anhydride (200 ml/216 g, 2.12 mol) is dripped thereinto slowly and portionwise. The reaction mixture is stirred at 50-70° C. for at least 1 hour then 1-(3-nitrophenyl)propan-1-one (150 g, 0.837 mol) and acetic anhydride (200 ml/216 g, 2.12 mol) suspension is added. The reaction mixture is stirred at about 70° C. for 16 hours, then conversion is monitored using HPLC. When the conversion is >90% about 200 ml of solvent are distilled under vacuum and 600 ml of ethanol are added. The obtained suspension is cooled to 20-25° C. and allowed to stir for 3 hours. Then it is filtered and washed with 300 ml of acetone. About 210 g of almost colourless solid and with HPLC purity >99% are obtained. The wet product is suspended in water (600 ml), t-butyl-methylether (600 ml) and the pH is adjusted to 10-12 with 28% sodium hydroxide. The two phases are stirred for about 30 minutes then they are separated. The organic phase is concentrated to oily residue. About 182 g of slightly yellowish oil (about 92% yield) with HPLC purity >99% are obtained.

Provenance & Evidence