Potassium Carbonate → 6-Methoxy-1,2,3,4-tetrahydroquinolin-2-one

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Reaction Conditions

Reaction Steps

To 6-hydroxy-3,4-dihydro-2(1H)-quinolinone (90.8 g, 0.56 mol, 1 equiv) in CH3CN (2 L) was added potassium carbonate (230.67 g, 1.67 mol, 3 equiv). The mixture was stirred for 1 h at 25° C., then Mel (75 g, 0.53 mol, 0.95 equiv) was added and the mixture was maintained at 60° C. for 12 hours. The mixture was filtered and the filtrate was taken to a residue under reduce pressure. The crude 6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone was directly use to the next step. (128 g, crude) 1H NMR (400 MHz, DMSO) δ, 2.34-2.38 (m, 2 H), 2.79 (t, 2 H, J=7.2 Hz), 3.65 (s, 3 H), 6.67 (m, 1H), 6.72-6.75 (m, 2 H), 9.86 (br, 1 H). This procedure was reproduced multiple times to prepare >300 g quantities of 6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone.

Provenance & Evidence