Hydrochloric Acid → 1-(3,5-Dimethylanilino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

With the exclusion of moisture, 100 mg (0.825 mmol) of 3,5-dimethyl-aniline are dissolved in 4 ml of ethanol, and 196 μl (0.784 mmol) of HCl (4N in dioxane) are added. After the addition of 200 mg (0.785 mmol) of 1-chloro-4-[(pyridin-4-yl)-methyl]-isoquinoline, the mixture is heated for 8 hours at 90° C. Concentration by evaporation is then carried out; the residue is taken up in 4 ml of water, 1 ml of saturated ammonia solution and 20 ml of CH2Cl2, and the organic phase is separated off, dried with Na2SO4 (anhydrous) and concentrated by evaporation again. Column chromatography (SiO2; ethyl acetatelhexane 3:1) and crystallisation from ethyl acetate/hexane yield the title compound: m.p. 156-158° C.; 1H NMR (DMSO-d6) 9.00 (s, HN), 8.54 (d, 1H), 8.42 (d, 2H), 8.00 (s, 1H), 7.80 (d, 1H), 7.65 (m, 2H), 7.50 (s, 2H), 7.26 (d, 2H), 6.64 (s, 1H), 4.25 (s, 2H), 2.27 (s, 6H); FAB-MS: (M+H)+=340; Anal. calc. (C23H21N3.0.1H2O) C 80.95%, H 6.26%, N 12.31%; found C 80.9%, H 6.2%, N 12.4%.

Herkunft & Nachweise