Sodium Hydroxide → (N,N-diethylaminomethyl)-2-pyridone

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Reaction Steps

The 5-bromomethyl-2-pyridone was taken up in diethyl amine and the solution refluxed for 1 hour. The solution was then treated with 10% sodium hydroxide at 0° C. and washed with chloroform. The aqueous phase was treated with hydrochloric acid to a pH of 6.0 and extracted with chloroform/methanol (5:1). The solution was dried over Na2SO4 and the solvent was then evaporated. The product, (N,N-diethylaminomethyl)-2-pyridone, was obtained in 34% yield. HRMS: m/e, M+ found; 180.1251, 20.8%. Calc. for C10H16N2O; 180.1263, −6.3 ppm. 1H NMR (ppm): 13.1 (broad, 1H, NH), 7.49 (dd, J3-4=9.2 Hz, J4-6=2.4 Hz, 1H, C(4)H), 7.25 (d, J4-6=2.4 Hz, 1H, C(6)H), 6.55 (d, J3-4=9.2 Hz, 1H, C(3)H), 3.30 (s, 2H, CH2O), 2.45 (q, J=7.1 Hz, 4H, N (CH2CH3)2), 1.00 (t, J=7.1 Hz, 6H, N (CH2CH3)2). IR (cm−1): 1660 (vs), υ (C═O).

Provenance & Evidence