Sodium Hydroxide → HCID 58909332, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of sodium hydroxide (228 mg, 5.7 mmol) in water (2.5 mL) was added bromine (94 μL, 1.84 mmol) dropwise. After stirring for 5 min at 0° C., amide 16 (336 mg, 1.5 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 20 min and then heated at 75° C. for 5 h. The reaction mixture was diluted with water and extracted with methylene chloride. The organic layer was washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give a yellow solid. Purification by flash column chromatography (silica, 95:5 methylene chloride/methanol) gave amine 17 (288 mg, 98%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.35 (s, 1H), 2.79 (d, J=7.2 Hz, 2H), 2.08 (m, 1H), 1.13 (m, 1H), 1.06–0.97 (m, 8H).

Provenance & Evidence