Triethylamine → 8,9-Dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one

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Reaction Steps

Synthesis of N-(quinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodo-5,6-dimethoxybenzamide (8d). Oxalyl chloride (2.1 g, 16.2 mmol) was added to a solution of 3,4-dimethoxy-6-iodobenzoic acid (1.5 g, 4.87 mmol) in anhydrous methylene chloride (40 mL), and the stirred mixture was refluxed for 4 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 40 mL of anhydrous methylene chloride, and this solution was added to a solution of 7d (870 mg, 4.05 mmol) and triethylamine (4.0 g, 40.0 mmol) in methylene chloride (30 mL), and the resulting mixture was stirred at reflux for 2 hours. The reaction mix was cooled and washed with saturated sodium bicarbonate (3×75 mL), and extracted with 5% aqueous HCl (4×100 mL). The combined aqueous extracts were basified with 30% NaOH and then extracted with chloroform (3×75 mL). Combined organic extracts were then dried (MgSO4) and evaporated to give 1.45 g of the amide, in 73% yield; 1H NMR (CDCl3) δ 2.23 (s, 6H), 2.63 (m, 2H), 3.07 (s, 3H), 3.68 (s, 3H), 3.93 (m, 1H), 4.62 (m, 1H), 6.26 (s, 1H), 7.00 (s, 1H), 7.44 (d, 1H, J=4.4), 7.69 (m, 2H), 8.11 (m, 2H), 8.75 (d, 1H, J=4.4); 13C NMR (CDCl3) δ 45.6, 47.0, 55.3, 56.0, 56.7, 82.5, 110.2, 121.6, 122.8, 125.8, 127.6, 130.0, 130.5, 130.6, 133.8, 146.9, 148.1, 149.6, 149.8, 150.8, 169.8; IR (CHCl3) 1650;

Provenance & Evidence