Borane → HCID 59807142, compound

Participants

Reaction Steps

A solution of 1-(2-(dimethylamino)ethyl)-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (0.8 g, 2.88 mmol) was treated with a solution of 1M borane in THF (28.8 mL, 28.80 mmol). The solution was heated at reflux for 6 hours then stirred at room temperature overnight. After this time, the mixture was cooled to 0° C. and quenched with methanol (20 mL). The mixture was concentrated, dissolved in methanol (20 mL), and heated at reflux for 4 hours. The reaction was concentrated and the residue was subjected to silica gel chromatography using a gradient of 1.5-5% 2M NH3 in MeOH/CH2Cl2 to give a yellow oil (565 mg, 74.6%). 1H-NMR (CDCl3) δ 7.96 (dd, J=2.7, 8.7 Hz, 1H), 7.91 (d, J=2.7 Hz, 1H), 6.75 (d, J=9.0 Hz, 1H), 3.44-3.39 (m, 2H), 3.37-3.33 (m, 2H), 2.88-2.85 (m, 2H), 2.55-2.51 (m, 2H), 2.29 (s, 6H), 1.85-1.78 (m, 4H). MS (ESI): 264.2 (M+1).

Provenance & Evidence