Sodium Hydroxide → HCID 67278943, compound

Participants

Reaction Steps

NaHB(OAc)3 (15.1 g, 0.0714 mmol) was added under vigorous stirring in portions to a solution of 2,3-dichlorobenzaldehyde (10 g, 0.057 mmol) and pyrrolidine (5.97 mL, 0.0714 mmol) in CH2Cl2 (200 mL). The reaction mixture was vigorously stirred overnight. Then 5N NaOH (50 mL) was added, and the layers were separated. The product was extracted from the aqueous layer with CH2Cl2 (2×50 mL). The combined extracts were washed with 5N NaOH (50 mL), water, brine, dried with anhydrous Na2SO4, and evaporated. The residue was distilled in vacuum to give title compound (10.5 g, 90%) as a colorless liquid (bp 80-84° C./0.5 mmHg). LC/MS data: 229.9, 230.9, 231.9 (M+H) (calculated for C11H13Cl2N 230.14). 1H NMR data (DMSO-d6): δ 7.52 (dd, 1H, J1=1.5 Hz, J2=7.8 Hz), 7.46 (dd, 1H, J1=1.5 Hz, J2=7.8 Hz), 7.33 (t, 1H, J=7.8 Hz), 3.70 (s, 2H), 2.46-2.52 (m, 4H), 1.66-1.75 (m, 4H).

Provenance & Evidence