Sodium Hydroxide → O-Benzylhydroxylamine

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A solution of O-benzyl hydroxylamine was prepared by dissolving 2 g of sodium hydroxide (0.05 mol) and 8 g of O-benzyl hydroxylamine hydrochloride (0.05 mol) in 50 mL of 50% ethanol-water. To this solution was added 6.15 g of 2-formyl-3-hydroxypyridine (0.05 mol). The mixture was stirred for 3 h at room temperature. The precipitate was then filtered and air dried to yield 10.3 g (90.3%) of pure product; m.p. 64°-65° C. 1H NMR (CDCl3) d: 9.72 (s, 1H, OH); 8.37 (s, 1H, CH=N); 8.13 (d of d, J=2H, J=4 Hz, 1H); 7.33 (m, 7H) 5.17 (s, 2H, CH2). Anal. Calcd. for C13H12N2O2 : C, 68.41; H, 5.30; N, 12.27. Found: C, 68.34; H, 5.32; N, 12.21.

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