Sodium Azide → (8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine

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Reaction Steps

Prepared according to Procedure E using 8-chloro-3-(chloromethyl)-2-(2-chloro-phenyl)quinoline (0.685 g, 2.12 mmol) and sodium azide (1.10 g, 17 mmol, 8 eq) in DMF (10 mL). The resulting intermediate was submitted to trimethyl phosphine (1.0M) in THF (2.5 mL, 2.5 mmol, 1.2 eq) in THF (8 mL) and water (2 mL). (8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine was obtained as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.62 (1 H, s), 8.05 (1 H, dd, J=8.6, 1.2 Hz), 8.00 (1 H, dd, J=7.4, 1.2 Hz), 7.63-7.73 (2 H, m), 7.47-7.62 (3 H, m), 3.90 (1 H, s), 3.75 (1 H, s) Mass Spectrum (ESI) m/e=303.1 and 305.0 (M+1)

Provenance & Evidence