Phosphorus oxychloride → 1-(2-Methylphenyl)-4-chloro-6-methylpyrrolo[3,2-c]quinoline

HRID 1416680Notes

Reaction equation

HRID 1416680 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]([CH3:21])[C:14]=3[NH:13][C:12](=O)[C:11]=2[CH:10]=[CH:9]1.P(Cl)(Cl)([Cl:25])=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]([CH3:21])[C:14]=3[N:13]=[C:12]([Cl:25])[C:11]=2[CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 157498281-(2-Methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline

Product 1

HCID 157498291-(2-Methylphenyl)-4-chloro-6-methylpyrrolo[3,2-c]quinoline

Procedure

1-(2-methylphenyl)-4-oxo-6-methyl-4,5-dihydro pyrrolo[3,2-c]quinoline (1.16 g, 4.0 mmol) was dissolved in 10 ml of phosphoryl chloride (POCl3) and heated for 2 hours. The reaction mixture was stirred at room temperature for 30 minutes after cooling and addition of ice water. The reaction mixture was extracted with methylene chloride (20 ml×3). After washing with water (15 ml×3), the organic layer was dried by anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain 1.12 g of desired compound as an oil in 91% of yield.

Workup

  1. temperatureheated for 2 hours
  2. temperatureafter cooling
  3. extractionThe reaction mixture was extracted with methylene chloride (20 ml×3)
  4. washAfter washing with water (15 ml×3)
  5. dry with materialthe organic layer was dried by anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-921f0e052b0e4d37ac4200c333b9eaa4
Source dataset
uspto-grants-1999_06
Patent number
US05914402

Reaction notes

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