Tetrahydrofuran → 7-(4-Fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700502Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.Cl.[NH2:17][CH2:18][C:19]#[C:20][CH3:21].O1CCCC1>C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][C:10]3[N:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:11]=3[C:12](=[O:14])[CH2:13]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 220 °C

Procedure

To a mixture of 5-(4-fluorophenyl)cyclohexane-1, 3-dione (0.98 g), 1-amino-2-butyne hydrochloride (0.5 g), molecular sieves 4A (2 g) and tetrahydrofuran (20 ml) was added triethylamine (0.48 g), and the mixture was refluxed for 14 hours and cooled. Insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was stirred for 6 hours at 220° C. and cooled, to which were added ethyl acetate and sodium hydrogen carbonate solution. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtoAc/hexane) to give oil of 7-(4-fluorophenyl)-4methyl-5,6,7,8-tetrahydroquinolin-5-one (0.35 g).

Workup

temperaturethe mixture was refluxed for 14 hours
temperaturecooled
filtrationInsoluble materials were filtered off
customUnder reduced pressure, the solvent was evaporated
temperaturecooled, to which
additionwere added ethyl acetate and sodium hydrogen carbonate solution
washThe organic layer was washed with water and saturated brine
dry with materialdried with magnesium sulfate
concentrationconcentrated under reduced pressure
customthe residue was purified with silica gel column chromatography (EtoAc/hexane)

Sources & evidence

ORD record: ord-7b1d9882db1e45fab35f7d280fdeb31f
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350749B1

Reaction notes

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