Dimethyl Sulfide → 6-(Methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (75 g of, 0.34 mol, 1 equiv) in THF (1L) was added BH3.DMS (10 M, 150 mL, 1.5 mol, 4.4equiv) dropwise at 25° C. After the addition, the mixture was stirred for 6 h at 60° C. The reaction was cooled and quenched with excess MeOH, concentration under reduced pressure and purified via chromatography on SiO2 t afford 6-(methyloxy)-7-nitro1,2,3,4-tetrahydroquinoline (51.5 g, 73% yield). 1H NMR (400 MHz, DMSO) δ 1.73-1.80 (m, 2 H), 2.71 (t, 2 H, J=6.4 Hz), 3.13-3.16 (m, 2 H), 3.75 (s, 3H), 5.83(br, 1 H), 6.88(s, 1 H), 6.95(s, 1 H).

Provenance & Evidence