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

HRID 1416675Notes

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:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>C1(O)C=CC=CC=1.O>[CH3:17][C:18]1[CH:19]=[C:20]([N:21]2[C:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH3:16])[C:4]=4[NH:3][C:2](=[O:1])[C:11]=3[CH2:12][CH2:13]2)[CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 190 °C

Procedure

4-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline (217 mg, 1.0 mmol) was dissolved in 7 ml of phenol in a pressure tube and 3-methylaniline (268 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 190° 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, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 230 mg of desired compound as solid in 76% 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
concentrationconcentrated under reduced pressure
customThe residue was purified with ethyl acetate as eluent by silica gel chromatography

Sources & evidence

ORD record: ord-70bfec361ec64afaafaeb0f1bbfd0f80
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914402

Reaction notes

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