Acetaldehyde → HCID 57244807, compound

Participants

Reaction Steps

Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino]benzoate (Compound 8, 80 mg, 0.22 mmol) was dissolved in a 10% acetic acid in acetonitrile solution (2.0 mL). The solution was treated with acetaldehyde (0.10 mL, 1.80 mmol) and then sodium cyanoborohydride (18 mg, 0.29 mmol) and the reaction mixture was stirred at room temperature for 1.5 hours. 1M aqueous NaOH was added until pH=6 and the solution was extracted with ether (2×), washed with brine, and dried (Na2SO4). The filtered solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes) to give the title compound (71 mg, 83%) as an oil.

Provenance & Evidence