O-Toluidine → 1-(2-Methylphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416671Notes

Reaction equation

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

Participants

Conditions

Temperature: 250 °C

Procedure

4-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline (217 mg, 1.0 mmol) was dissolved in 10 ml of diethylene glycol in a pressure tube and 2-methylaniline (267 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 250° C. for 15 hours. The reaction mixture was diluted with 20 ml of salt water and the aqueous layer was extracted with methylene chloride (15 ml×3). After washing with water (15 ml×3), the organic layer was dried by anhydrous magnesium sulfate and filtered, amd concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 235 mg of desired compound as solid in 77% of yield.

Workup

extractionthe aqueous layer was extracted with methylene chloride (15 ml×3)
washAfter washing with water (15 ml×3)
dry with materialthe organic layer was dried by anhydrous magnesium sulfate
filtrationfiltered
concentrationamd concentrated under reduced pressure
customThe residue was purified with ethyl acetate as eluent by silica gel chromatography

Sources & evidence

ORD record: ord-f02d30bc5efb4078a32b8105d5d744b4
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914402

Reaction notes

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