6-Methyl-3-pyridinecarboxaldehyde → HCID 46842009, compound

Participants

Reaction Steps

A mixture of 6-methylnicotinaldehyde (0.36 g, 3.0 mmol), 2-amino-N-(4-(methylthio)phenyl)benzamide (3.0 mmol), and anyhydrous CuCl2 (0.80 g, 6.0 mmol) in anyhydrous EtOH was refluxed for 6 hours. After concentration in vacuo, the residue was redissolved in EtOAc and washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 0% to 20% MeOH in CH2Cl2, followed by 40% to 100% of 92:7:1 CHCl3/MeOH/concentrate NH4OH in CH2Cl2, afforded the title compound (19%). 1H-NMR (300 MHz, DMSO-d6): δ8.42 (s, 1H), 8.20 (d, J=7.9 Hz, 1H), 7.87-7.97 (m, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.56-7.73 (m, 2H), 7.31 (d, J=8.3 Hz, 2H), 7.10-7.26 (m, 3H), 2.43 (s, 3H), 2.41 (s, 3H). MS (APCI) m/z: 360 (M+H)+.

Provenance & Evidence