Pyridine-3-carboxaldehyde O-methyloxime
Vittorio E. Caprio, Michael W. Jones and Margaret A. Brimble*
Department of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand, Fax: (+64 9) 3737599 ; E-mail: [email protected]
* Author to whom correspondence should be addressed.
Received: 8 December 2000 / Accepted: 15 December 2000 / Published: 25 March 2001
The general part of the experimental section [1] has been presented elsewhere. Methoxylamine hydrochloride (858 mg, 10.3 mmol) and potassium carbonate (2.58 g, 18.7 mmol) were added to a solution of pyridine-3-carboxaldehyde (1 g, 9.34 mmol) in ethanol (15 mL) under nitrogen at room temperature and the mixture was stirred for 2 h [2]. Water (20 mL) and dichloromethane (20 mL) were then added and the organic and aqueous phases separated. The aqueous phase was extracted with dichloromethane (3 x 15 mL) and the organic extracts were combined. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography using ethyl acetate as eluent afforded the title compound (1.25 g, 98%) as a pale yellow oil.
IR (cm-1, neat): 3394b, 2968m, 2938m, 1610m, 1591m, 1564m, 1421m, 1413m, 1056s, 1039s.
1H NMR (200 MHz, CDCl3): 4.01 (3H, s, OCH3), 7.31 (1H, dd, J5,6 4.8 and J5,4 7.8 Hz, H5), 7.97 (1H, ddd, J5,4 7.8, J4,6 1.8 and J4,2 1.8 Hz, H4), 8.08 (1H, s, HC=N), 8.61 (1H, dd, J6,4 1.8 and J6,5 4.8 Hz, H6), 8.74 (1H, d, J2,4 1.8 Hz, H2).
13C NMR (50 MHz, CDCl3): 62.0 (CH3, OCH3), 123.4 (CH, C5), 128.1 (quat., C3), 133.1 (CH, C4), 145.2 (CH, C6), 148.4 (CH, C2), 150.4 (CH, HC=N).
EI-MS: 136 (M+, 100%), 105 (M+-OCH3, 16%), 78 (M+-C2H4NO, 82%), 51 (49%).
Anal. Calc. for C7H8N2O, 136.0610; found M+, 136.0637.
Reference
1. Brimble, M. A.; Duncalf, L. J. Molecules
2000, 5, 162-166.
2. Goti, A.; Cicchi, S.; Fedi, V.; Nannelli,
L.; Brandi, A. J. Org. Chem. 1997, 62, 3119-3125.
Sample availability: available from the authors.
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