3-Nitrobenzaldehyde → HCID 19894043, compound

Participants

Reaction Steps

7-(3-methylisoxazol-5-yl)heptylacetoacetate (1.967 g, 0.007 l mol) was added to a solution of methyl-β-aminocrotonate (0.805 g, 0.007 mol) and m-nitrobenzaldehyde (1.057 g, 0.007 mol) in isopropanol (35 mL). The reaction mixture was heated under reflux for 12 h and then concentrated under reduced pressure. The residual oil was purified by elution from a silica gel column using dichloromethane-hexane (9:1, v/v) as eluant to give 3-[7-(3-methylisoxazol-5-yl)heptyloxycarbonyl]-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine (60%) as a pale yellow thick oil. IR (neat) 3330 (NH) and 1701 and 1676 (CO2R)cm-1, NMR (CDCl3) 1.20-1.40 (m, 6H, --(CH2)3), 1.56-1.74 (m, 4H, --(CH2)2), 2.30 (S, 3H, Me), 2.39 (S, 3H, Me), 2.72 (t, J =9 Hz, 2H, CH2 -Het), 3.70 (S, 3H, CO2Me), 3.99-4.16 (m, 2H,--OCH2), 5.14 (S, 1H, H-4), 5.89 (S, 1H, Het-H), 7.06 (S, 1H, NH), 7.38-8.14 (m, 4H, H-2 , H-4', H-5', H-6'). Analysis found: C, 63.48; H, 6.45; N, 7.99. Required: C, 63.39; H, 6.50; N, 8.21 (C27H33N3O7). ##STR6##

Provenance & Evidence