Tetrahydrofuran → HCID 53392262, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-(diethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (1 g, 3.43 mmol) and 1M BH3 in THF (17.16 ml, 17.16 mmol) was stirred at room temperature overnight. After this time, the reaction was cooled to 0° C. then treated with methanol (25 mL) dropwise with caution. The mixture was stirred at 0° C. for 10 minutes then concentrated on the rotovap to give a yellow solid. This compound was dissolved in 40 mL methanol and heated at reflux for 3 hours. After cooling, the solvent was evaporated and the resulting yellow brown residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in methanol/95% CH2Cl2 to give a bright yellow residue (0.87 g, 91%). 1H-NMR (CDCl3) δ 7.96 (dd, J=2.7, 9.0 Hz, 1H), 7.85-7.84 (m, 1H), 6.51 (d, J=9.0 Hz, 1H), 3.47 (t, J=5.4 Hz, 4H), 2.74 (t, J=6.3 Hz, 2H), 2.68-2.59 (m, 6H), 1.99-1.91 (m, 2H), 1.05 (t, J=6.9 Hz, 6H). MS (ESI): 278.2 (M+1).

Provenance & Evidence