Hydrogen Bromide → HCID 22253387, compound

Participants

Reaction Steps

To a solution of 2-(2,4,6-trimethylphenoxy)-N4-(1-ethylpropyl)-6-methyl-pyridine-3,4-diamine (640 mg, 1.95 mmol) and 7 ml of 48% hydrobromic acid was added a solution of sodium nitrite (146 mg, 2.11 mmol) in 2 ml of water dropwise over 5 min at 0° C. The resulting mixture was treated with cuprous bromide Cu(I)Br (145 mg, 1.01 mmol) and then heated at reflux for 15 min. The mixture was cooled to room temperature and diluted with water, basified with ammonium hydroxide and extracted twice with ethyl acetate. The organic layer was dried and concentred to give 710 mg (93% yield) of the title compound as brown crystals, which was further recrystallized from isopropyl ether to give the title compound as golden crystals. 1H NMR (CDCl3) δ 6.92(s,2H), 6.84(s,1H), 4.5(m,1H), 2.40(s,3H), 2.32(s,3H), 2.13(s,6H), 2.0–2.4(m,4HO, 0.83(t,6H)ppm.

Provenance & Evidence