Pyridine → HCID 14497416, compound

Participants

Reaction Steps

4-Methoxyphenylhydrazine hydrochloride [35.0 grams (g), 0.20 moles] was added to CH3OH [50 milliliters (ml)] containing pyridine (20 ml). An additional amount of CH3OH (25 ml) was added to the thick resulting slurry. 1-(4-Chlorophenyl)-6-hydroxyhexan-1,3-dione (48.2 g, 0.20 moles), was added neat, followed by more CH3OH (25 ml). The slurry was stirred at room-temperature for 1.5 hours, after which time the mixture was concentrated and taken up in CHCl3 (300 ml). The CHCl3 solution was washed with 1N HCl (300 ml), dried (Na2SO4), filtered, and concentrated. The oil was decolorized (Norit) in hot diethyl ether (Et2O) (300 ml). The Et2O solution was cooled, and crystallization from Et2O (300 ml) afforded 2 (49.4 g). From the filtrate was obtained additional 2 (9.28 g), total yield 91%, mp 87.5°-88°. NMR (CDCl3) 1.7-2.3 (m, 2H, CH2CH2CH2), 2.55 (brs, 1H, OH), 2.80 (t, 2H, J=7 Hz, CH2), 3.75 (t, 2H, J=6 Hz, CH2O), 3.77 (s, 3H, OCH3), 6.28 (s, 1H, C4 -H), 6.93 (ABq, 4 H, J=12, 9, 4-OMe-C6H4), 6.9-7.3 (m, 4H, 4-Cl--C6H4); IR (KBr) 3320, 2920, 1495; MS, m/e 342 (M+), 312, 298 (100%);

Provenance & Evidence