Synthesis of ethyl 5-cyano-6-hydroxy-2-methyl-4-(1-naphthyl)-nicotinate

Tetrahedron Letters

Volumn 49, Issue 23, 2008, Pages 3757-3761

  Zhou, Yongchang ^a   Kijima, Tatsuro ^a   Kuwahara, Shunsuke ^b   Watanabe, Masataka ^b   Izumi, Taeko ^a  

^a YAMAGATA UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYL 5 CYANO 6 HYDROXY 2 METHYL 4 (1 NAPHTHYL)NICOTINATE; NICOTINIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 43049108363     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.027     Document Type: Article

References (27)

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19. Typical procedure: To a mixture of methanol (30 ml) and toluene (30 ml), ethyl acetoacetate (5.20 g, 40 mmol), 1-naphthaldehyde (6.24 g, 40 mmol), methyl 2-cyanoacetate (3.96 g, 40 mmol) and Ammonium acetate (3.24 g, 42 mmol) were added. The mixture was heated to reflux under stirring for 24 h. The resulting solution were workuped by azeotropic distillation to separate off all toluene, to which water (3 ml) was added. The resulting solvent was kept for refluxing for 24 h and then allowed to cool to room temperature. The light yellow crystals were formed and filtered to give the title compound, and then purified by recrystallization from chloroform-ethyl acetate.
20. -1): 3441, 2226, 1733, 1431, 1324, 1288.
21. 3, δ, ppm): 19.53, 52.20, 76.80, 103.53, 114.15, 115.27, 124.36, 125.16, 125.73, 126.66, 127.25, 128.77, 129.81, 130.27, 133.08, 133.35, 152.94, 160.91, 162.61, 165.16.
22. 3: C 72.28; H 4.85; N 8.43. Found: C 72.42; H 4.90; N 8.36.
23. Crystal data for 5c: CCDC 677844.
24. 4) and evaporated in vacuo to give the title compound 6 as a pale yellow oil.
25. 3), 4.52 (s, 1H, {double bond, long}CH).
26. 3 (0.06 g, 5 mol %) in ethanol (5 mL), 1-naphthaldehyde (2 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 5 h. The resulting yellow solid was filtered and recrystallized to give the pure title compound 7 as a slight yellow solid.
27. +].