(8-Methoxyquinolin-5-yl)methanol → 8-Methoxyquinoline-5-carbaldehyde

Participants

Reaction Steps

5-Hydroxymethyl-8-methoxyquinoline (6.5 g, 34 mmol) from Step 1 was dissolved in 250 mL of DCM and treated with 24 g of manganese dioxide. After stirring for 24 h, the mixture was treated with an additional 6 g of manganese dioxide and stirred for 24 h. The mixture was filtered through a pad of Celite, and the filtrate was concentrated under vacuum to afford 6 g of the title compound as a brown solid. 1H NMR (CDCl3) δ 10.2 (s, 1 H), 9.69 (d, 1 H), 9.01 (d, 1 H), 8.01 (d, 1H), 7.61 (dd, 1H), 7.16 (d, 1H), 4.19 (s, 3H).

Provenance & Evidence