2-Methyl-4-methoxyaniline → 220853-65-6

HRID 849193Notes

Reaction equation

HRID 849193 reaction equation
O=[C:2]1[C:11]2[CH2:12][CH2:13]O[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:15][C:16]([F:19])([F:18])[F:17])[C:4]=2[NH:3]1.[CH3:20][C:21]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:22]=1[NH2:23]>C(O)COCCO.[Cl-].[Na+].O>[CH3:20][C:21]1[CH:27]=[C:26]([O:28][CH3:29])[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[N:3]=[C:2]([NH:3][CH2:4][CH2:5][OH:15])[C:11]=2[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 10858582HCID 10858582, compound

Product 1

HCID 10113707220853-65-6Yield 160.3%

Reagents, catalysts & solvents 2

HCID 8117Diethylene GlycolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
250 °C

Procedure

4-Oxo-6-trifluoromethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline(5.0 g, 19 mmol) was dissolved in diethylene glycol(30 ml) and 2-methyl-4-methoxyaniline(6.1 ml, 46 mmol) was added. The reaction mixture was refluxed at 250° C. for 15 hours, diluted in brine(20 ml), and the aqueous layer was extracted with dichloromethane(15 ml) for 3 times. The organic layer was washed with water(15 ml) for 3 times, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 6.6 g of desired compound as solid in 91% of yield.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane(15 ml) for 3 times
  2. washThe organic layer was washed with water(15 ml) for 3 times
  3. dry with materialdried over 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-a32dc391e7634bd2b01512dcd754c897
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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