Allylamine → HCID 2832220, compound

Participants

Reaction Conditions

Reaction Steps

Step 1′ A 3-L, three-necked, round-bottomed flask equipped with a mechanical stirrer, a nitrogen inlet adapter, and a 500-mL pressure-equalizing addition finnel fitted with a glass stopper was purged with nitrogen. The flask was charged with allylamine (K) 33.9 g (0.593 mol), 50 mL of ethyl acetate, triethylaamine 60.0 g (0.593 mol), and then cooled with an ice-water bath. The addition funnel was charged with 3-nitro-benzoyl chloride (J) 100.0 g (0.539 mol) and 230 mL ethyl acetate, and this solution was then added dropwise to the reaction mixture over 1 h while the reaction mixture was maintained at 0° C. The reaction mixture was stirred at 0° C. for 3 h and then filtered. The filtrate was transferred to a separatory finnel and washed with 150 mL of a 10% (by volume) HCl aqueous solution, 100 mL of saturated sodium chloride solution, dried over magnesium sulfate, and the solvent volume was reduced to one-third the original volume under reduced pressure. The clear solution was cooled to 0° C. overnight. The resulting yellow solid was collected by filtration and dried in a vacuum oven at 50° C. for 6 h to afford 89.4 g (80% yield) of N-allyl-3-nitrobenzamide (L) as a yellow solid.

Provenance & Evidence