Potassium Carbonate → 6-Bromo-1-methyl-1,2,3,4-tetrahydroquinoxaline

Participants

Reaction Conditions

Reaction Steps

4-bromo-N1-(2-chloroethyl)-N1-methylbenzene-1,2-diamine 1 (3.1 g, 0.012 mol) was dissolved in DMF (6 ml), Potassium carbonate (3.3 g, 0.024 mol) was added. The reaction was stirred at 100° C. for 2 h. The mixture was partitioned between water and EtOAc (2×30 mL) The combined organic layers was concentrated and purified by flash chromatography eluted with EtOAc to give 1.9 g, (69.6%) of 6-bromo-1-methyl-1,2,3,4-tetrahydroquinoxaline. 1H NMR (300 MHz, DMSO-d6) δ 6.50-6.45 (m, 2H), 6.31 (d, J=8.2 Hz, 1H), 5.79 (s, 1H), 3.29 (s, 4H). 3.07 (t, J=2.4 Hz, 2H), 2.71 (s, 3H), LCMS-ESI+ (m/z): [M+H]+ calcd for C9H11BrN2:226.01; found 226.96.

Provenance & Evidence