2-Ethylaniline → HCID 19369810, compound

HRID 849175Notes

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][C:16]([F:19])([F:18])[F:17])[C:4]=2[NH:3]1.[CH2:20]([C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24])[CH3:21]>C(O)COCCO.[Cl-].[Na+].O>[CH2:20]([C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[N:24]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([O:15][C:16]([F:19])([F:18])[F:17])[C:4]=3[N:3]=[C:2]([NH:3][CH2:4][CH2:5][OH:15])[C:11]=2[CH2:12][CH2:13]1)[CH3:21]

Participants

Conditions

Temperature: 250 °C

Procedure

4-Oxo-6-trifluoromethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline(7.0 g, 25.8 mmol) was dissolved in diethylene glycol(30 ml) and 2-ethylaniline(6.7 g, 51 mmol) was added under nitrogen. The reaction mixture was refluxed at 250° C. for 15 hours. The reaction mixture was diluted in brine(20 ml), then the aqueous layer was extracted with dichloromethane(15 ml) for 3 times. The organic layer was washed with water(15 ml) for 3 times, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate as eluent to obtain 5.1 g of desired compound as solid in 53% of yield.

Workup

extractionthe aqueous layer was extracted with dichloromethane(15 ml) for 3 times
washThe organic layer was washed with water(15 ml) for 3 times
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography with ethyl acetate as eluent

Sources & evidence

ORD record: ord-46ef3b26750e467c99504d7f5f5bd5aa
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011044

Reaction notes

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