O-Toluidine → HCID 11132128, compound

HRID 1416676Notes

Reaction equation

HRID 1416676 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][C:16]([F:19])([F:18])[F:17])=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[CH3:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23]>C(O)COCCO.O>[CH3:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[N:23]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[NH:3][C:2](=[O:1])[C:11]=2[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 7242O-ToluidineHCID 131721283HCID 131721283, compound

Product 1

HCID 11132128HCID 11132128, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
250 °C

Procedure

4-Oxo-6-trifluormethoxy-2,3-dihydrofuro[3,2-c] quinoline (272 mg, 1.0 mmol) was dissolved in 10 ml of diethylene glycol and 2-methylaniline (267 μl 1.0 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, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 298 mg of desired compound as solid in 83% of yield.

Workup

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

Sources & evidence

ORD record
ord-29db0502e70848e4b3a225fefbe98eb7
Source dataset
uspto-grants-1999_06
Patent number
US05914402

Reaction notes

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