Sodium Chloride → N-(2-dimethylamino-ethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide

Participants

Reaction Steps

49 mg (0.36 mmol) of 1-hydroxybenzotriazole, 69 mg (0.36 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 73 μL (0.66 mmol) of N-methylmorpholine and 40 μL (0.36 mmol) of N,N-dimethylethylenediamine are added to 75 mg (0.33 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 75) suspended in 0.7 ml of anhydrous dimethylformamide. The reaction mixture is stirred overnight at room temperature. The mixture is diluted with ethyl acetate (20 mL) and a saturated solution of sodium chloride (20 mL). The two phases are separated and the aqueous phase is extracted with ethyl acetate (3×20 mL). The organic phases are combined, washed with n aqueous solution of potassium carbonate (10%) (3×40 mL), water (40 mL) and a saturated solution of sodium chloride (50 mL), dried over magnesium sulfate and evaporated. The residue obtained is triturated in diethyl ether to give 13 mg (13%) of N-(2-dimethylamino-ethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide in the form of a light brown solid.

Provenance & Evidence