2,4-Dimethoxyaniline → HCID 178493409, compound

HRID 1710478Notes

Reaction equation

HRID 1710478 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[F:12][C:13]([F:23])([F:22])[C:14](=O)[CH2:15][C:16](OCC)=[O:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:12][C:13]([F:23])([F:22])[C:14]1[CH:15]=[C:16]([OH:17])[C:6]2[C:4](=[C:3]([O:2][CH3:1])[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=2)[N:5]=1

Participants

5

Reactant 3

HCID 176522,4-DimethoxyanilineHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 178493409HCID 178493409, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
130 °C

Procedure

2,4-Dimethoxyaniline (30 g) was dissolved in benzene (400 mL), and ethyl trifluoroacetoacetate (34 mL) and p-toluenesulfonic acid monohydrate (3.7 g) were added. The mixture was refluxed for 21 hr. The reaction solution was concentrated under reduced pressure, and a saturated a aqueous sodium hydrogen carbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The extract solution washed with saturated brine, dried and concentrated under reduced pressure. 75% Polyphosphoric acid (150 mL) was added to the residue and the mixture was stirred at 130° C. for 2 hr. The reaction solution was poured onto ice, and the mixture was extracted with ethyl acetate. The extract solution washed successively with a saturated a aqueous sodium hydrogen carbonate solution, 1 mol/L hydrochloric acid and saturated brine, dried and concentrated under reduced pressure. Ethanol was added to the residue and the precipitate was filtered off. The filtrate was concentrated under reduced pressure to give 2-trifluoromethyl-4-hydroxy-6,8-dimethoxyquinoline (12 g) as an oil.

Workup

  1. temperatureThe mixture was refluxed for 21 hr
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additiona saturated a aqueous sodium hydrogen carbonate solution was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract solution washed with saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. addition75% Polyphosphoric acid (150 mL) was added to the residue
  9. additionThe reaction solution was poured onto ice
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe extract solution washed successively with a saturated a aqueous sodium hydrogen carbonate solution, 1 mol/L hydrochloric acid and saturated brine
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. additionEthanol was added to the residue
  15. filtrationthe precipitate was filtered off
  16. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e6602f8b1c2b40ba9be476e65306edb0
Source dataset
uspto-grants-2010_09
Patent number
US07790725B2

Reaction notes

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