4-(Benzyloxy)-2-methylaniline → 1-(2-Methyl-4-benzyloxyphenyl)-4-[(2-hydroxyethyl)amino]-6-beta,beta,beta-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 849216Notes

Reaction equation

O=[C:2]1[C:11]2[CH2:12][CH2:13]O[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:4]=2[NH:3]1.[CH2:21]([O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[C:31]([CH3:36])[CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)COCCO.O>[CH3:36][C:31]1[CH:30]=[C:29]([O:28][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:35]=[CH:34][C:32]=1[N:33]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:4]=3[N:3]=[C:2]([NH:3][CH2:4][CH2:5][OH:15])[C:11]=2[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 250 °C

Procedure

4-Oxo-6-β,β,β-trifluoroethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline(5.7 g, 20.0 mmol) was dissolved in diethylene glycol(70 ml) and crude 4-benzyloxy-2-methyl aniline(5.6 g, 26.0 mmol) was added. The reaction mixture was refluxed at 250° C. for 15 hours. The reaction mixture was dissolved in water, extracted with dichloromethane, and the organic layer was washed with water for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography(ethyl acetate:dichloromethane=1:1) to obtain 4.5 g of desired compound as solid in 47% of yield.

Workup

extractionextracted with dichloromethane
washthe organic layer was washed with water for 3 times
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography(ethyl acetate:dichloromethane=1:1)

Sources & evidence

ORD record: ord-eac70824543a4d88831844bc2ef6e005
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011044

Reaction notes

Loading…