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

HRID 1416672Notes

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.C[C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20].C(O)[CH2:26][O:27]CCO>O>[CH3:26][O:27][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 of 2-methylaniline (282 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 layer with water (15 ml×3), the organic layer was dried with anhydrous magnesium sulfate and filtrated to be concentrated under reduced pressure. The residue was purified with ethyl acetate as a development solution according to silica gel chromatography to obtain 260 mg of desired compound as solid in 81% of yield.

Workup

additionwas added under nitrogen
extractionthe aqueous layer was extracted with methylene chloride (15 ml×3)
dry with materialAfter layer with water (15 ml×3), the organic layer was dried with anhydrous magnesium sulfate
filtrationfiltrated
concentrationto be concentrated under reduced pressure
customThe residue was purified with ethyl acetate as a development solution

Sources & evidence

ORD record: ord-9bc7731f26ce419184f45d1b5a4a7c9a
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914402

Reaction notes

Loading…