Triethylamine → HCID 59299897, compound

Participants

Reaction Steps

To a suspension of 1,2-diacetyl-4-methoxymethylene-1,4-dihydro-2H-cinnolin-3-one (0.18 g, 0.66 mmol) and 5-(aminomethyl)-2-methoxyphenol hydrochloride (0.13 g, 0.66 mmol) in tetrahydrofuran (5 mL) is added triethylamine (0.21 mL). After the addition of a few drops of N,N-dimethylformamide, the reaction mixture is stirred for five days at room temperature. The solvent is then evaporated under reduced pressure to give a maroon oil, which is then purified by via semi-preparative HPLC (Prodigy ODS3 column, 40% MeCN/60% water/0.01% trifluoroacetic acid to 70% acetonitrile over 1 hour at 10 mL/min) to give (4Z)-1,2-diacetyl-4-{[(3-hydroxy-4-methoxybenzyl)amino]methylene}-1,4-dihydrocinnolin-3(2H)-one (0.14 g, 54%) as a straw-colored foam, which is crushed to a powder.

Provenance & Evidence