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4-(2,3-dimethylphenyl)-1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In methanol; ethanol;
EXAMPLE 17 4-(2,3-Dimethylphenyl)-1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester 1-Methyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine (6.36 g.), 5.93 g. of methyl-3-aminocrotonate (97percent), 11 g. of <strong>[5779-93-1]2,3-dimethylbenzaldehyde</strong> and 100 ml. of ethanol were refluxed for 3 hours. The mixture was filtered while hot and then left standing overnight. The precipitated solid was separated by filtration. The solid was suspended in methanol and saturated with hydrogen chloride. The solvent removed in vacuo. The residue was recrystallized from ethanol to obtain the title compound as the hydrochloride, m.p. 244°-247° C. dec. Analysis for: C20 H24 N2 O3.HCl: Calculated: C, 63.73; H, 6.68; N, 7.43; Cl, 9.41. Found: C, 63.85; H, 6.77; N, 7.38; Cl, 9.33.
4-(2,3-dimethylphenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In methanol; ethanol;
EXAMPLE 20 4-(2,3-dimethylphenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester A mixture of 16.2 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 9.2 g. of methyl-3-aminocrotonate, 11.6 g. of <strong>[5779-93-1]2,3-dimethylbenzaldehyde</strong> and 180 ml. of ethanol was heated at reflux for 3 hours. The solvent was removed in vacuo and the residue was recrystallized from ethanol to obtain 14 g. of solid, m.p. 208°-211° C. The solid was suspended in methanol and saturated with hydrogen chloride. The solvent was removed in vacuo. The residue was recrystallized from methanol to obtain the title compound as the hydrochloride, m.p. 238°-239° C. d. Analysis for: C26 H28 N2 O3.HCl: Calculated: C, 68.94; H, 6.45; N, 6.18; Cl, 7.83. Found: C, 68.78; H, 6.51; N, 6.41; Cl, 7.77.
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