HCID 19369769, compound → HCID 19369812, compound

HRID 849224Notes

Reaction equation

HRID 849224 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[C:14]=3[NH:13][C:12](=O)[C:11]=2[CH:10]=[CH:9]1>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:25])[F:26])[C:14]=3[N:13]=[C:12]([NH:13][CH2:14][CH2:15][OH:21])[C:11]=2[CH:10]=[CH:9]1

Participants

3

Reactant 1

HCID 19369769HCID 19369769, compound

Product 1

HCID 19369812HCID 19369812, compoundYield 169.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-(2-Methylphenyl)-4-oxo-6-β,β,γ,γ,γ-pentafluoropropyloxy-4,5-dihydropyrrolo[3,2-c]quinoline(1.5 g, 3.8 mmol) was dissolved in phosphoryl chloride(15 ml), then the resultant was stirred 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), 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 1.5 g of desired compound as solid in 94% of yield.

Workup

  1. customAfter removing the excess phosphoryl chloride
  2. distillationby simple distillation
  3. additionthe residue was poured into iced water
  4. stirringstirred at room temperature for 30 minutes
  5. extractionIt was extracted 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-6293ee2fbfda47838f86bd5c1a2cdcc6
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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