Hydrochloric Acid → 6-Acetyl-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1840872Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][C:5]2([CH3:14])[CH3:13].C([Sn](CCCC)(CCCC)[C:20]([O:22]CC)=[CH2:21])CCC.Cl>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:20]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][C:5]2([CH3:14])[CH3:13])(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 6-bromo-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (Intermediate 4, 270 mg, 1.06 mmol) in 5 ml of THF was first degassed by bubbling with argon for 30 min. Tributyl(1-ethoxyvinyl)tin (766 mg, 2.12 mmol) and PdCl2(PPh3)2 (37mg, 0.05 mmol) were added. After stirring at 80° C. for 18 h, the mixture was cooled to room temperature and 3 mL of 10% HCl was added. The mixture was then stirred for another 30 min before extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chormatography (50:50 hexane/ethyl acetate) yielded the title compound as a white solid (154 mg, 67% yield).

Workup

customby bubbling with argon for 30 min
temperaturethe mixture was cooled to room temperature
stirringThe mixture was then stirred for another 30 min
extractionbefore extracted with ethyl acetate (3×10 mL)
washThe combined organic layer was washed with brine (1×10 mL)
dry with materialdried (MgSO4)
concentrationconcentrated at reduced pressure
customPurification by flash chormatography (50:50 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-2284227a08b34a7f97e9de14f83ae5b1
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683092B1

Reaction notes

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