HCID 19369788, compound → HCID 19369826, compound

HRID 849184Notes

Reaction equation

HRID 849184 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=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][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=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:25])[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

Participants

3

Reactant 1

HCID 19369788HCID 19369788, compound

Product 1

HCID 19369826HCID 19369826, compoundYield 162.4%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-(2,3-Dimethylphenyl)-4-oxo-6-trifluoromethoxy-2,3,4,5-tetrahydro-pyrrolo[3,2-c]quinoline(4.4 g, 11.8 mmol) was dissolved in phosphoryl chloride(10 ml). 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), and stirred for 30 minutes. The resultant 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 4.0 g of desired compound as solid in 87% 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. extractionThe resultant 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-78fa2b69f43248b7a1cceb28c12f182d
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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