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ChemicalBook CAS DataBase List C-Quinolin-2-yl-methylamine dihydrochloride
18004-62-1

C-Quinolin-2-yl-methylamine dihydrochloride synthesis

6synthesis methods
-

Yield: 90%

Reaction Conditions:

with hydrogenchloride in ethanol at 0 - 90;

Steps:

4.2.9 Quinolin-2-ylmethanamine bischlorohydrate 15
First method: To a solution of N,N-diBocquinolin-2-ylmethanamine 14 (5 g, 14mmol) in EtOH (25 mL), a solution of EtOH·HCl 4N (52.5 mL, 210 mmol) was added at 0 °C. The solution was allowed to return at ambient temperature and stirred for 3 h. Then, the mixture was heated at 90 °C up to the complete disappearance of the of N,N-diBoc-quinolin-2-ylmethanamine 14 (approxim. 30 min). The mixture was evaporated to dryness to give a white solid, which was purified through a silica gel column chromatography (CH2Cl2/CH3OH: 95/5+1% Et3N). 90% yield; 1H NMR (300 MHz, CDCl3) 4.47 (2H, m, CH2), 7.71 (1H, m, CHar), 7.81 (1H, m, CHar), 7.94 (1H, m, CHar), 8.10 (2H, m, CHar), 8.61 (1H, m, CHar), 8.88 (2H, s large, NH), 9.91 (1H, s large, NH); 13C NMR (75 MHz, CDCl3) 42.29, 120.62, 126.78, 127.26, 128.22, 131.06, 139.06, 144.94, 149.37, 153.69.

References:

Maj, Anna M.;Suisse, Isabelle;Hardouin, Christophe;Agbossou-Niedercorn, Francine [Tetrahedron,2013,vol. 69,# 44,p. 9322 - 9328]

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