|Oxidation of Primary & Secondary Amines||Bookmark|
General Procedure for the Oxidation of Primary & Secondary amines using m-chloroperbenzoic acid.
m-Chloroperbenzoic acid (4.1g, 0.02mol, 85% pure) is dissloved in 30 mls of 1,2-dichloroethane in a three-neck flask equipped with a condenser and a pressure-equalising dropping funnel. The amine (0.005 mol) in 3-5 mls of 1,2-dichloroethane solvent is added drop-wize to the refluxing m-Chloroperbenzoic acid/1,2-dichloroethane solution. Refluxing temperature 83oC for 3 hours.
After the addition of the amine and refluxing time, the reaction mixture is cooled, filtered and washed with three 50 ml portions of 1M sodium hydroxide solution and dried over anhydrous magnesium sulphate. The removal of the 1,2-dichloroethane solvent by distillation (rotary) gives a crude nitroalkane. Purification of the crude crude nitroalkane with vacuum distillation. Yields vary, approx 62 %.
Oxidation of n-propylamine and higher alkane amines give nitroalkane at approx 62 %.
[Note] Nitromethane and nitroethane form sodium water-soluable salts with 1M sodium hydroxide solution.
|Re: Oxidation of Primary & Secondary Amines||Bookmark|
m-Iodoperbenzoic acid also works
Do Your Part To Win The War