Sodium Hydroxide → 1-(2-(Dimethylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine

Participants

Reaction Steps

A solution of 6-amino-1-(2-(dimethylamino)ethyl)-3,4-dihydroquinolin-2(1H)-one (1.3 g, 5.57 mmol) in 10 mL anhydrous THF was added dropwise to a cooled suspension of 1M LiAlH4 in THF (22.3 mL, 22.3 mmol). The suspension was stirred at room temperature for 1 day. After this time, the mixture was cooled to 0° C. and treated with 5 mL 1N NaOH dropwise with rapid stirring. After stirring for 30 minutes, the suspension was treated with Na2SO4 and filtered. The filter cake was rinsed with 10% 2M NH3 in MeOH/CH2Cl2 (100 mL total). The filtrate was concentrated and the dark residue was subjected to flash chromatography on silica gel using 5-10% 2M NH3 in MeOH/CH2Cl2 to give a dark viscous oil (930 mg, 76.2%). 1H-NMR (CDCl3) δ: 6.49 (brs, 2H), 6.40 (s, 1H), 3.34-3.30 (m, 2H), 3.30 (br s, 2H), 3.21 (t, J=5.7 Hz, 2H), 2.68 (t, J=5.7 Hz, 2H), 2.49-2.44 (m, 2H), 2.28 (s, 6H), 1.95-1.87 (m, 2H).

Provenance & Evidence