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

HRID 1014292Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[C:13](=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:13][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

additionMel (75 g, 0.53 mol, 0.95 equiv) was added
temperaturethe mixture was maintained at 60° C. for 12 hours
filtrationThe mixture was filtered
customto prepare >300 g quantities of 6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone

Sources & evidence

ORD record: ord-ab16a2d3e3f5465ea97ff78d46682ce8
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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