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1 Synthesis of N-(4-amino-2-methyl-6-quinolyl)-2-[(4-ethylphenoxy)methyl]-benzamide hydrochloride
To the reaction mixture was added an aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate, and the solvent was evaporated. The obtained crude product was dissolved in ethanol and treated with active charcoal, and the solvent was evaporated. The obtained residue was dissolved in ethyl acetate and 1N hydrochloric acid-ether solution was added. The resulting precipitate was collected by filtration. The obtained solid was heated and dried under reduced pressure to give the title compound (1.06 g, 59%, pale-yellow crystals). Elemental analysis for C26H25N3O2.HCl Calculated; C, 69.71%; H, 5.85%; N, 9.38%. Found; C, 69.77%; H, 5.78%; N, 9.41%.
133 Synthesis of N-(4-amino-2-methyl-6-quinolyl)-2-[(4-ethylphenoxy)methyl]-benzamide hydrochloride monohydrate
Example 133 Synthesis of N-(4-amino-2-methyl-6-quinolyl)-2-[(4-ethylphenoxy)methyl]-benzamide hydrochloride monohydrate To crude crystals of N-(4-amino-2-methyl-6-quinolyl)-2-[(4-ethyl-phenoxy)methyl]benzamide hydrochloride (24.0 g, 53.7 mmol) obtained in the same manner as in Example 1 was added ethanol (120 ml) and the mixture was heated to 55-60° C. for dissolution. This solution was filtrated and to the filtrate was dropwise added water (120 ml) with stirring under heating at 55-60° C. This reaction mixture was cooled to room temperature and the resulting precipitate was filtrated.
A Examples
A) Compound 1 (N-quinolylbenzamide derivative) N-(4-Amino-2-methyl-6-quinolyl)-2-[(4-ethylphenoxy)methyl]benzamide hydrochloride (N-(4-Amino-2-methylquinolin-6-yl)-2-[(4-ethylphenoxy)methyl]benzamide hydrochloride)