Methylamine → 6-Bromo-2-methylamino-1-nitronaphthalene

Participants

Reaction Steps

A solution of 6-bromo-2-methoxy-1-nitronaphthalene (5.64 g, 20 mmol) in 100 ml of dry N,N-dimethylformamide saturated with methylamine was stirred in a stoppered flask at 80° C. for 4 h. During the reaction period the mixture was saturated twice with a further quantity of methylamine. The cooled mixture was poured into 1 1 of ice/water. After stirring for 1 h, the orange solid was collected by filtration and washed with water, and dried in vacuo over phosphorus pentoxide affording 5.43 g (96%) of the title compound. M.p. 169°-170 ° C.: 1H-NMR (CDCl3): 3.11 (d, J=5 Hz, 3H, CH3), 7.00 (d, J=9 Hz, 1H, ArH), 7.45-7.78 (m, 3H, ArH), 8.60 (d, J=9 Hz, 1H, ArH), 8.7 (broad, 1H, NH).

Provenance & Evidence