87% |
With formaldehyd; In water; for 12h;Reflux; |
Synthesis of synthesis of H2[O2NN]BuMeEtPy (H2L) A mixture containing 2-tert-butyl-4-methylphenol (1.6425 g, 10 mmol), 2-tert-butyl-4-ethylphenol (1.7827 g, 10 mmol), aminomethylpyridine (1.0814 g, 10 mmol), and 37% aqueous formaldehyde (1.6232 g, 20 mmol) in water (25 mL) was refluxed with stirring for 12 h. Cooling to room temperature produced a white precipitate which was collected, and recrystallized from ethanol. Drying under vacuum yielded H2[O2NN]BuMeEtPy (87%). Anal. Calc. for C31H42N2O2: C, 78.48; H, 8.86; N, 5.91. Found C, 78.26; H, 8.74; N, 5.87%. 1H NMR (400 MHz, CDCl3) delta10.50 (s, 2H), 8.71 (d, J = 4.8 Hz, 1H), 7.71 (t, J = 7.6 Hz, 1H), 7.28 (dd, J = 12.1, 5.3 Hz, 1H), 7.13 (d, J = 7.8 Hz, 1H), 7.03 (d, J = 7.4 Hz,2H), 6.79 (t, J = 11.3 Hz, 2H), 3.81 (d, J = 25.8 Hz, 6H), 2.56 (q, J = 7.6 Hz, 1.5H), 2.25 (s, 3H), 1.41 (s, 18H), 1.22 (q, J = 7.9 Hz, 2H). 13C NMR (101 MHz, CDCl3) delta156.13, 154.11, 153.92, 148.16, 137.36, 137.16, 133.65, 129.02, 128.99, 127.57, 127.19, 127.07, 126.05, 123.71, 122.52, 122.11, 122.00, 56.42, 56.19, 55.31, 34.86, 34.80, 29.62, 28.29, 20.77, 15.94. UV-Vis [CH3CN, lambdamax/nm (epsilon/mol-1 cm-1: 282 (3.98 x 103). |