Sodium Hydroxide → HCID 178484203, compound

Participants

Reaction Steps

To a stirred solution of phenyl 2-(8-fluoro-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate (400 mg, 0.884 mmol) in Ethanol (11 ml) was added sodium hydroxide (354 mg, 8.84 mmol) as a solution in Water (5.5 ml). The resulting mixture was stirred at reflux and monitored by TLC. After 3 h, the reaction mixture showed some formation of product, and some starting material. Due to the formation of some side product, the reaction was stopped, diluted with water and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in 0-10% (2M NH3 in MeOH) in dichloromethane, giving the desired N-(8-fluoro-1-(2-(methylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (67 mg, 0.202 mmol, 22.80% yield).1NMR (DMSO-d6) δ 7.71 (d, J=3, 1H); 7.58 (d, J=5 Hz, 1H); 7.07 (dd, J=5 Hz, 3 Hz, 1H); 6.48-6.43 (m, 2H); 6.41 (brd, J=15 Hz, 1H); 6.34 (s, 1H); 3.09 (m, 4H); 2.73-2.64 (m, 4H); 2.31 (s, 3H); 1.77-1.72 (m, 2H). EI-MS (m/z, %): 332 (M+, 9), 288 (100).

Provenance & Evidence