HCID 19369835, compound → HCID 19369810, compound

HRID 849176Notes

Reaction equation

HRID 849176 reaction equation
[CH2:1]([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)[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH2:1]([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:25])([F:24])[F:26])[C:15]=3[N:14]=[C:13]([NH:14][CH2:15][CH2:16][OH:22])[C:12]=2[CH2:11][CH2:10]1)[CH3:2]

Participants

3

Reactant 1

HCID 19369835HCID 19369835, compound

Product 1

HCID 19369810HCID 19369810, compoundYield 228.8%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-(2-Ethylphenyl)-4-oxo-6-trifluoromethoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline(2.5 g, 6.7 mmol) was dissolved in phosphoryl chloride(10 ml), then the 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 3.2 g of desired compound as solid in 85% of yield.

Workup

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

Sources & evidence

ORD record
ord-a6a6a55ec0174e57a9d5d4a01cf73ea1
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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