Hydrochloric Acid → HCID 68981936, compound

Participants

Reaction Steps

To a mixture of 2-chloro-4-methyl-5-nitropyridine (5.44 g, 26.3 mmol) and dibenzylamine (5.04 mL, 26.3 mmol) in toluene (13.1 mL) was added sodium carbonate (5.58 g, 52.6 mmol). After stirring under a nitrogen atmosphere under reflux for 36 h, the reaction mixture was filtered to remove the sodium carbonate. The filtrate was concentrated to provide the crude material as a light orange oil. The crude oil was dissolved in methylene chloride and treated with 2 N HCl. The resulting precipitate was filtered off and discarded. The filtrate was washed with 2 N HCl and the acidic layers were back-extracted with methylene chloride. The combined extracts were washed with saturated NaHCO3, dried over Na2SO4, filtered and concentrated to provide 2-(dibenzylamino)-5-nitro-4-methylpyridine (8.97 g, 102% theoretical) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ2.53 (3H, s), 4.85 (4H, s), 6.27 (1H, s), 7.19-7.37 (10H, m), 9.05 (1H, s).

Provenance & Evidence