HCID 19369783, compound → HCID 19369805, compound

HRID 849180Notes

Reaction equation

HRID 849180 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][C:23]([F:26])([F:25])[F:24])[C:15]=3[NH:14][C:13](=O)[C:12]=2[CH2:11][CH2:10]1>P(Cl)(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][C:23]([F:24])([F:26])[F:25])[C:15]=3[N:14]=[C:13]([NH:9][CH2:4][CH2:3][OH:2])[C:12]=2[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 19369783HCID 19369783, compound

Product 1

HCID 19369805HCID 19369805, compoundYield 160.9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-(2-Methoxyphenyl)-4-oxo-6-trifluoromethoxy-2,3,4,5-tetrahydro-pyrrolo[3,2-c]quinoline(3.0 g, 8.0 mmol) was dissolved in phosphoryl chloride(10 ml), then reaction mixture was refluxed for 2 hours. After removing the excess phosphoryl chloride by simple distillation, the residue was poured into iced water, neutralized with aqueous solution of sodium hydroxide(1N), stirred at room temperature for 30 minutes, and extracted with dichloromethane(20 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 by silica gel chromatography to obtain 2.7 g of desired compound as solid in 85% of yield.

Workup

  1. customreaction mixture
  2. temperaturewas refluxed for 2 hours
  3. customAfter removing the excess phosphoryl chloride
  4. distillationby simple distillation
  5. additionthe residue was poured into iced water
  6. extractionextracted with dichloromethane(20 ml) for 3 times
  7. washThe organic layer was washed with water(15 ml) for 3 times
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-77d89a63e4ef4f6b88d1a276abfcbdc6
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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