Hydrochloric Acid → 1-(4-(Furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-2-aminoethyl oxime

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Reaction Steps

1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone (compound 1) was prepared according to the method as described in Example 4 of U.S. Pat. No. 6,750,223 B2. The thus obtained compound 1 (0.30 g, 1 mmol), 2-aminoethoxyamine.HCl (0.28 g, 2.5 mmol), and K2CO3 (0.69 g, 5.0 mmol) were added into EtOH (10 mL). The resultant mixture was subjected to reflux for 4 hours (TLC monitoring), followed by evaporation under reduced pressure. The residue thus acquired was dissolved in CH2Cl2 (50 mL). The CH2Cl2 layer was washed sequentially with H2O and brine, was dried using Na2SO4, and was subjected to an evaporation treatment. The resultant residue was purified via flash column chromatography (MeOH/CH2Cl2=1/50), followed by recrystallization from EtOH. The title compound 13a as a light yellow solid (0.45 g, 96% yield) was obtained.

Provenance & Evidence