Benzaldehyde → HCID 10364246, compound

Participants

Reaction Steps

N-(2-Aminoethyl)-3-(2-methylquinolin-4-ylamino)benzamide (50). A mixture of methyl ester 49 (2.0 g, 6.8 mmol) and ethylenediamine (30 mL) was heated at 110° C. for 2 hours before it was poured into ice water (300 mL). The precipitate was filtered and dried under high vaccum to give 50 (2.0 g, 91%) as an off-white solid, which was used without further purification. Step 2. N-(2-Benzylaminoethyl)-3-(2-methylquinolin-4-ylamino)benzamide. A solution of amine 50 (0.22 g, 0.68 mmol) and benzyaldehyde (0.07 mL, 0.08 mmol) in EtOH (3.0 mL) was heated at reflux overnight before it was allowed to cool to room temperature. Sodium borohydride (0.04 g, 0.80 mmol) was added and the reaction was stirred at room temperature for 1 hour. The mixture was mixed with 2N NaOH (3.0 mL), brine (2.0 mL), and extracted with 7:3 CH2Cl2/MeOH (3×5.0 mL). The combined organic layers were dried (K2CO3) and concentrated under reduced pressure. The residue was purified by flash chromatrography (SiO2, gradient elution, 3:1 hexanes/EtOAc to 7:3 CH2Cl2/MeOH) to yield the desired product (0.15 g, 62%) as a pale yellow solid.

Provenance & Evidence