Water → Acetamide, N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl)-

HRID 1242929Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].CI.O.[C:19](OCC)(=O)C>O1CCCC1>[CH3:19][N:4]([C:5]1[CH:14]=[CH:13][C:12]2[C:11](=[O:15])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=1)[C:1](=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

6-Acetamido-1-tetralone (13.7 g, 67.4 mmol) was dissolved in tetrahydrofuran (40 ml). Sodium hydride(oil)(2.40 g, 101 mmol) was added to the solution, which was refluxed with heating for 2.5 hours. After cooling, methyl iodide(20 ml)was added to the reaction mixture, which was stirred at 40° C. for 15 hours. The reaction mixture was poured into a cold water, and extraction was conducted using ethyl acetate. The extract was washed with 1N hydrochloric acid and 1 N aqueous sodium hydroxide solution. The ethyl acetate layer was concentrated. The residue was purified by alumina column chromatography (development solvent; ethyl acetate:n-hexane=50:50 ˜100:0). The eluent was concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate-diisopropyl ether, to give the titled compound(8.3 g).

Workup

temperaturewas refluxed
temperaturewith heating for 2.5 hours
temperatureAfter cooling
washThe extract was washed with 1N hydrochloric acid and 1 N aqueous sodium hydroxide solution
concentrationThe ethyl acetate layer was concentrated
customThe residue was purified by alumina column chromatography (development solvent; ethyl acetate:n-hexane=50:50 ˜100:0)
concentrationThe eluent was concentrated under reduced pressure
customThe resulting residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-1fc583316a6144c18b3de09b89a850a2
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115750B1

Reaction notes

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