Sodium Hydroxide → HCID 59807132, compound

Participants

Reaction Steps

A solution of 6-amino-1-(2-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (245 mg, 0.90 mmol) in 10 mL anhydrous THF was cooled to 0° C. and treated with dropwise addition of 1M LiAlH4 in THF (2.7 mL, 2.7 mmol). The suspension was stirred at room temperature overnight. After this time, the mixture was cooled to 0° C. and treated with 1.5 mL 1N NaOH dropwise with rapid stirring. After stirring for 30 minutes, the suspension was diluted with 10 mL CH2Cl2 was treated with Na2SO4. The suspension was filtered and the solid was rinsed with 20 mL 5% 2M NH3 in MeOH/CH2Cl2. The filtrate was concentrated and the dark residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a dark viscous oil (136 mg, 58.4%). 1H-NMR (CDCl3) δ: 6.84 (br, 2H), 6.41 (br, 1H), 3.48 (dd, J=4.2, 14.4 Hz, 1H), 3.24-3.19 (m, 4H), 3.91 (dd, J=14.4, 4.2 Hz, 1H), 2.69-2.67 (m, 6H), 1.95-1.79 (m, 7H), 1.14 (d, J=6.6 Hz, 3H).

Provenance & Evidence