3-Pyridinecarboxaldehyde → HCID 43182253, compound

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Reaction Steps

A solution of 4-bromo-α-methylbenzylamine (1.5 g, 7.7 mmol), 3-pyridinecarboxaldehyde (0.8 g, 7.5 mmol), and sodium triacetoxyborohydride (2.25 g, 10.5 mmol) in 60 ml of 1,2-dichloroethane was stirred at room temperature for 18 h. The solution was diluted with dichloromethane and washed twice with a saturated sodium bicarbonate solution, once with water, and once with brine. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 8.70 (m,2H), 7.85 (m,1H), 7.67 (d,2H,J=8 Hz), 7.45 (d,2H,J=8 Hz), 7.43 (m,1H), 3.95 (q,1H,J=8 Hz), 3.83 (q,ABX,2H), 1.57 (d,3H,J=8 Hz). MS calcd. 291.2; MS (M+1) 292.1.

Provenance & Evidence