N-methylpropyn-2-ylamine → N-methyl-N-propargyl-9-anthramide

Participants

Reaction Steps

A solution of 20.8 g of 9-anthroyl chloride in 100 ml of tetrahydrofuran is added at 10°-15° to a solution of 14.2 g of N-methylpropargylamine in 50 ml of tetrahydrofuran. After stirring at room temperature for 3 hours, the solvent is removed and the residue is stirred with methylene chloride and 5% aqueous sodium bicarbonate solution. The methylene chloride layer is dried and concentrated to give 23.3 g of crude N-methyl-N-propargyl-9-anthramide as an oil. H nmr spectrum: τ 1.7-2.9 (m, 9); 5.4 (d, 2.5 Hz, 1.3); 6.4 (d, 2.5 Hz, 0.7); 6.7 (s, 0.9); 7.4 (s, 2.1); 7.7 (t, 2.5 Hz, 0.7) and 8.0 (t, 0.3). The spectrum shows the presence of two rotamers.

Provenance & Evidence