3-Nitroaniline → 4-(3-Nitrophenyl)morpholine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-nitroaniline (42)(5.52 g, 40.00 mmol) in anhydrous dimethylacetamide (15 ml) was added 2-bromoethylether (7.52 ml, 60.00 mmol) and N,N-diisopropylethylamine (13.94 ml, 80.0 mmol). The mixture was then heated to 120° C. for 6 hours. After this time the reaction was cooled to room temperature which saw the mixture take the form of a slurry. The slurry was dissolved in CH2Cl2 (80 ml) and washed with 0.2 M HCl (3×30 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo to give a brown semi-solid residue that was triturated with Et2O to give the desired product (8.33 g, 79.7%) in suitably clean form to be used without any further purification. m/z (LC-MS, ESP): 209 [M+H]+, R/T=3.46 mins

Provenance & Evidence