Selenium Dioxide → 7-Chloroquinoline-4-carbaldehyde

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Selenium dioxide (4.52 g; 40.3 mmol) in a mixture of 25 ml of dioxane and 6 ml of water was added in a dropwise fashion to 7-chlorolepidine (6; 6.50 g; 36.6 mmol) in 25 ml of dioxane to 65°-75° C. The temperature was raised to 85° C. and maintained there with stirring for 6 hours. After cooling, the-mixture was filtered through Celite™ and concentrated. The crude material was purified on a flash column, eluting with 10% ethyl acetate/hexane to obtain 5.24 g (74%) of aldehyde 7 as a yellow solid. 1H NMR (CDCl3): δ 7.68 (d, 1H); 7.79 (d, 1H); 8.19 (d, 1H); 9.01 (dd, 1H); 9.21 (m, 1H); 10.45 (s, 1H). IR (KBr): 1702, 1499, 1216, 1041, 900, 653 cm-1.

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