2,6-Lutidine → HCID 178468691, compound

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Reaction Steps

A solution of ethyl-4-amino-3-[3'-(N-tert-butyloxycarbonylamino)-1'-acetoxyiminopropyl]benzoate (2.8 g, 7.1 mmol) and 2,6-lutidine (0.83 ml, 7.1 mmol) in m-xylene (200 ml), was heated at reflux in Dean-Stark apparatus for 5 hours. The solution was then cooled to ambient temperature and the solvent evaporated in vacuo. The crude residue was purified by flash chromatography (eluent 1:1 petrol:ethyl acetate) to give the indazole (0.95 g, 67%) as a colourless oil. NMR (250 MHz, CDCl3) δ 1.42 (12H, m), 3.20 (2H, t, J=7 Hz), 3.65 (2H, m), 4.41 (2H, q, J=7 Hz), 5.09 (1H, br t), 7.44 (1H, d, J=9 Hz), 8.05 (1H, dd, J=9 and 2 Hz), 8.45 (1H, br s), 10.50 (1H, br s).

Provenance & Evidence