P-Anisidine → HCID 178487932, compound

HRID 1791952Notes

Reaction equation

HRID 1791952 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[F:10][C:11]([F:21])([F:20])[C:12](=O)[CH2:13][C:14](OCC)=[O:15].C(=O)([O-])O.[Na+]>P(=O)(O)(O)O>[F:10][C:11]([F:21])([F:20])[C:12]1[CH:13]=[C:14]([OH:15])[C:8]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:9]=2)[N:7]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 178487932HCID 178487932, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
110 °C

Procedure

4-Methoxyaniline (5.00 g) was dissolved in 75% phosphoric acid (20 mL) and ethyl trifluoroacetoacetate (7.48 g) was dropwise added thereto at 110° C. The mixture was stirred at 110° C. for 4 hr with heating. After allowing to cool, the reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 2-trifluoromethyl-4-hydroxy-6-methoxyquinoline (0.450 g).

Workup

  1. customat 110° C
  2. temperaturewith heating
  3. temperatureto cool
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe extract was dried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8809f565982e48bd9ed66429e37203cc
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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