Synthesis of methyl 2, 6-dimethyl-5-(1′, 2′-dioxo-2′-ethoxyethyl)-4-(3′-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

descriptionPublicationkeyboard_double_arrow_right Article 01 Sep 1990 English Publisher:Springer Science and Business Media LLCJournal:Archives of Pharmacal Research, volume 13, pages 257-260 (issn: 0253-6269, eissn: 1976-3786,

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Authors: Jungjin Suh; Youhwa Hong;

doi: 10.1007/bf02856531

Synthesis of methyl 2, 6-dimethyl-5-(1′, 2′-dioxo-2′-ethoxyethyl)-4-(3′-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

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Abstract

Hantzch’s type reaction of methyl acetopyruvate(2a), methyl 3-aminocrotonate(3) and 3-nitrobenzaldehyde(4) led to dimethyl 3-acetyl-6-methyl-4-(3′-nitrophenyl)-2,5-dicarboxylate(5a) and methyl 2,6-dimethyl-5-(1′, 2′-dioxo-2′-methoxyethyl)-4-(3′-nitrophenyl)-1,4-dihydropyridine-3-carboxylate(6a) in 26.7 and 9.2% yield, respectively. On the other hand, methyl 2,6-dimethyl-4-(3′-nitrophenyl)-1, 4-dihydropyridine 3-carboxylate(9) was acylated by ethyl oxaly chloride to give methyl 2,6-dimethyl-5-(1′,2′-dioxo-2′-ethoxyethyl)-4-(3′-nitrophenyl)-1,4-dihydropyridine-3-carboxylate(6b) in 76.8% yield.

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