Cl.[NH2:2][OH:3].[CH2:4]([C:8]1[CH:13]=[C:12]([C:14](=O)[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH:5]([CH3:7])[CH3:6].CO>O.[OH-].[Na+]>[CH2:4]([C:8]1[CH:13]=[C:12]([C:14](=[N:2][OH:3])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH:5]([CH3:7])[CH3:6]A solution of hydroxylamine hydrochloride (120 mg, 1.732 mmol) in water (0.5 mL) and 1 N aq. NaOH (1.2 mL) is added to 1-(2-isobutyl-6-methyl-pyridin-4-yl)-ethanone (276 mg, 1.44 mmol). The solution is stirred at 80° C. for 2 h and MeOH is added to maintain homogeneity of the mixture. The mixture is cooled to rt and the precipitate that forms is collected, washed with water and dried in vacuo to give 1-(2-isobutyl-6-methyl-pyridin-4-yl)-ethanone oxime (258 mg) as a white solid; 1H NMR (D6-DMSO): δ 0.88 (d, J=6.5 Hz, 6H), 1.98-2.10 (m, 1H), 2.13 (s, 3H), 2.45 (s, 3H), 2.56 (d, J=7.0 Hz, 2H), 7.22 (s, 1H), 7.27 (s, 1H), 11.54 (s, 1H).
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