Boron tribromide → HCID 21931653, compound

Participants

Reaction Steps

Under nitrogen, combined 1.3 g of 7-Methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (6.8 mmol) with 18 ml of CH2Cl2. Added 15 ml of 1.0 M boron tribromide in CH2Cl2 (15.0 mmol) dropwise over 3 minutes. Stirred reaction for 5 hours, poured over ice-H2O, slurried for 15 minutes and filtered 818 mg of off-white solid (68%). 1H NMR (400 MHz, CD3OD) δ 2.56 (2H, t, J=7.88 Hz), 2.78 (2H, t, J=6.85 Hz), 3.29 (3H, s), 6.45 (1H, d, J=8.09 Hz), 6.54 (1H, d, J=2.07 Hz), 6.98 (1H, d, J=8.09 Hz). M/z (APCI+) 178.0 (M+1). HPLC (aqueous 200 mM ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 uM, 125×4 mm column) 2.826.

Provenance & Evidence