ChemicalBook CAS DataBase List (Quinolin-7-yl)methanamin hydrochloride

(Quinolin-7-yl)methanamin hydrochloride synthesis

6synthesis methods

Product Name:(Quinolin-7-yl)methanamin hydrochloride
CAS Number:773092-54-9
Molecular formula:C10H10N2
Molecular Weight:158.2

773092-53-8
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773092-54-9
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Yield: 94%

Reaction Conditions:

with hydrogen;nickel in methanol under 760.051 Torr;

Steps:

21.E
E) Quinolin-7-ylmethanamine7-(Azidomethyl)quinoline (1.1 g, 5.7 mmol) was hydrogenated (1 atm) in the presence of Raney nickel (1.5 g, 26 mmol) in methanol (30 mL) until completion of the reaction. Catalyst was filtered off and the filtrate was concentrated under reduced pressure to a yellow oil which was dissolved in EtOAc (32 mL) and extracted with 1N hydrochloric acid (3×32 mL). The combined acidic aqueous phases were adjust to pH10 with 1N sodium hydroxide solution, and extracted with EtOAc (3×35 mL). The combined organic layers were dried over MgSO₄, filtered, and concentrated under reduced pressure to afford a white solid (0.89 g, 94%).¹H NMR (300 MHz, CD₃OD) 8.83 (d, J=4.2 Hz, 1H), 8.36 (d, J=7.8 Hz, 1H), 7.97 (s, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.64 (d, J=8.4 Hz, 1H), 7.52 (dd, J=7.8, 4.2 Hz, 1H), 4.05 (s, 2H).

References:

Wei, Zhi-Liang;O'Mahony, Donogh John Roger;Duncton, Matthew;Kincaid, John;Kelly, Michael G.;Wang, Zhan US2008/275037, 2008, A1 Location in patent:Page/Page column 33

346-55-4 Synthesis