Sodium Azide → 7-(Azidomethyl)-4-chloroquinoline-2-carbonitrile

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Reaction Steps

A mixture of 7-(bromomethyl)-4-chloroquinoline-2-carbonitrile (8.46 g, 30 mmol), sodium azide (2.15 g, 33 mmol) in EtOH (300 mL) was heated under reflux for 1 h. The mixture was then cooled to room temperature and evaporated to dryness. The crude material was purified by flash chromatography (eluting solvent: 100% CH2Cl2 to 5% acetone in CH2Cl2) to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.40 (d, 1H), 8.20 (m, 2H), 7.97 (d, 1H), 4.85 (s, 2H).

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