Sodium Azide → 4-Azido-5-chloropyridine-3-carbaldehyde

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Reaction Steps

A mixture of 4,5-dichloropyridine-3-carbaldehyde (6.78 g, 38.5 mmol) and sodium azide (2.62 g, 40.4 mmol) in DMF (25 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine (250 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane) to afford the title compound as a yellow solid (6.7 g, 96% yield). 1H NMR (400 MHz, CDCl3): δ 10.36 (s, 1H), 8.84 (s, 1H), 8.65 (s, 1H).

Provenance & Evidence