Water → 1-(2-Methyl-4-hydroxyphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416669Notes

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]([CH3:15])=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[NH2:16][C:17]1[C:18]([CH3:24])=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1.O>C(O)COCCO>[CH3:24][C:18]1[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:17]=1[N:16]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH3:15])[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-methyl-2,3-dihydrofuro[3,2-c]quinoline (201 mg, 1.0 mmol) was dissolved in 10 ml of diethylene glycol in a pressure tube and 4-amino-m-cresol (308 mg, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 250° C. for 15 hours. The reaction mixture was diluted in 20 ml of salt water and the aqueous layer was extracted by 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 210 mg of desired compound as solid in 81% of yield.

Workup

extractionthe aqueous layer was extracted by 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-b871a4f9229b4f3ca5577eac75106be6
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914402

Reaction notes

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