2-(2-Chlorophenyl)ethylamine → 2-Amino-5-cyanopyridine

Participants

Reaction Steps

1H-NMR (500 MHz, DMSO): δ (ppm). 8.74(1H, d, J=2.4Hz, H-6), 8.04(1H, dd, J=2.4, 9.2Hz, H-4), 7.20(1H, brs, NH2), 6.53(1H, d, J=9.2Hz, H-3 ) , 4.27 (2H, t, J=6.7Hz, OCH2CH2CH3), 1.7 5 (2H, m, OCH2CH2CH3) , 0.97 (3H, t, J=7.3Hz, OCH2CH2CH3). Propyl N-cyano-6-amino-3-pyridinecarboximidate (200 mg, 0.98 mmol) and 2-(2-chlorophenyl)ethylamine (170 mg, 1.09 mmol) were dissolved in a mixture of methanol (10 ml) and DMF (1.5 ml), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure and subjected to silica gel column chromatography (Wako Gel C-200, 25 g), and elution was conducted with chloroform:methanol (30:1) to give the title compound (250 mg, yield 85%) as colorless powder.

Provenance & Evidence