Naphthalene → 6-Cyclopropoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1244019Notes

Reaction equation

C1C2C(=CC=CC=2)C=CC=1.[Li].[C-]1C2C(=CC=CC=2)C=CC=1.[Li+].[CH3:23][N:24]1[C:33]2[C:28](=[CH:29][C:30]([O:34][C:35]3(SC4C=CC=CC=4)[CH2:37][CH2:36]3)=[CH:31][CH:32]=2)[CH2:27][CH2:26][C:25]1=[O:45]>C1COCC1.C(OCC)(=O)C.O>[CH:35]1([O:34][C:30]2[CH:29]=[C:28]3[C:33](=[CH:32][CH:31]=2)[N:24]([CH3:23])[C:25](=[O:45])[CH2:26][CH2:27]3)[CH2:36][CH2:37]1

Participants

Conditions

Temperature: -78 °C

Procedure

Naphthalene (1.0 g, 7.85 mmol) was dissolved in THF (7.5 ml) under nitrogen and freshly cut lithium metal (54 mg, 7.85 mmol) was added. The mixture was stirred at room temperature until a dark green solution of lithium naphthalenide was obtained. This solution was cooled to −78° C., then 1-Methyl-6-(1-phenylsulfanyl-cyclopropoxy)-3,4-dihydro-1H-quinolin-2-one (170 mg, 0.53 mmol) in THF was added over 1 minute. The reaction was stirred for 17 minutes and then water and ethyl acetate were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extract was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography using 30% ethylacetate/hexane to give the title compound (42 mg, 36% yield).

Workup

customwas obtained
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate
extractionThe combined organic extract
dry with materialwas dried (MgSO4)
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-8827436b32f2479e96c1c7ff30b565af
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119207B2

Reaction notes

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