HCID 19369787, compound → 220853-65-6

HRID 849194Notes

Reaction equation

HRID 849194 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:23][C:24]([F:27])([F:26])[F:25])[C:16]=3[NH:15][C:14](=O)[C:13]=2[CH2:12][CH2:11]1>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:23][C:24]([F:26])([F:25])[F:27])[C:16]=3[N:15]=[C:14]([NH:15][CH2:16][CH2:17][OH:23])[C:13]=2[CH2:12][CH2:11]1

Participants

3

Reactant 1

HCID 19369787HCID 19369787, compound

Product 1

HCID 10113707220853-65-6Yield 129.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-(2-Methyl-4-methoxyphenyl)-4-oxo-6-trifluoromethoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline(4.0 g, 10 mmol) was dissolved in phosphoryl chloride(10 ml). The reaction mixture was refluxed for 2 hours, and cooled. After removing the excess phosphoryl chloride by simple distillation, the residue was poured into iced water, neutralized with aqueous solution of sodium hydroxide (1N), and stirred at room temperature for 30 minutes. It was extracted with dichloromethane(20 ml) for 3 times, and 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 2.8 g of desired compound as solid in 70% of yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperaturecooled
  3. customAfter removing the excess phosphoryl chloride
  4. distillationby simple distillation
  5. additionthe residue was poured into iced water
  6. extractionIt was extracted 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-809713f4e75b4b6794ac3d26d3ef99bb
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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