Anthracene-9-carbonyl chloride → N-(Prop-2-YN-1-YL)anthracene-9-carboxamide

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Reaction Steps

A solution of 13.68 g of 9-anthroyl chloride in 30 ml of tetrahydrofuran is added at 10°-15° to a solution of 10 g of propargylamine in 60 ml of tetrahydrofuran. After stirring at room temperature for 4 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 14.54 g of crude N-propargyl-9-anthramide as a solid. An analytical sample (ethanol) had a melting point of 201°-202°; H nmr spectrum: τ 1.5-2.8 (m, 9); 3.7 (broad, 1); 5.7 (d of d, 2) and 7.7 (τ, 2.5 Hz, 1).

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