Sodium Hydroxide → HCID 59807075, compound

Participants

Reaction Steps

A solution of 1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (700 mg, 2.87 mmol) in 12 mL anhydrous THF was treated with LiAlH4 (218 mg, 5.73 mmol) portionwise. The suspension was stirred at room temperature for 1 day. After this time, the mixture was cooled to 0° C. and treated with 2 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 CH2Cl2 (150 mL total). The filtrate was concentrated and the residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a light yellow oil (563 mg, 85.1%). 1H-NMR (CDCl3) δ: 7.06-7.01 (m, 1H), 6.93 (d, J=7.2 Hz, 1H), 6.63-6.52 (m, 2H), 3.44 (t, J=7.5 Hz, 2H), 3.31 (t, J=5.7 Hz, 2H), 2.76-2.56 (m, 8H), 1.97-1.90 (m, 2H), 1.83-1.78 (m, 4H).

Provenance & Evidence