Benzyl Alcohol → HCID 67312948, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl alcohol (1.32 g, 12.2 mmol) in THF (15 mL) at room temperature was added sodium hydride (60% dispersion in mineral oil, 488 mg, 12.2 mmol). The mixture was stirred at room temperature for 0.5 h at which time 6-chloro-N-(4-ethylphenyl)-3-nitropyridin-2-amine (1.21 g, 4.03 mmol) was added. The mixture was heated in a sealed tube overnight at 65° C. The reaction vessel was cooled to room temperature and the mixture was quenched with saturated NaHCO3. The mixture was extracted with EtOAc and the organics were dried over MgSO4, filtered, and concentrated. Purification by silica gel chromatography (2% EtOAc in hexanes gradient to 15% EtOAc in hexanes) gave the title compound (987 mg) as a yellow solid. NMR (400 MHz, CDCl3) δ ppm 1.26 (t, J=7.6 Hz, 3H), 2.66 (q, J=7.6 Hz, 2H), 5.34 (s, 2H), 6.25 (d, J=9.1 Hz, 1H), 7.20 (d, J=8.4 Hz, 2H), 7.41-7.28 (m, 5H), 7.45 (d, J=8.4 Hz, 2H), 8.40 (d, J=9.1 Hz, 1H), 10.51 (broad s, 1H).

Provenance & Evidence