Phosphorus oxychloride → HCID 15749850, compound

HRID 1416678Notes

Reaction equation

HRID 1416678 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21]3[C:20]4[CH:19]=[CH:18][CH:17]=[C:16]([CH3:22])[C:15]=4[NH:14][C:13](=O)[C:12]=3[CH2:11][CH2:10]2)=[C:5]([CH3:24])[CH:4]=1.P(Cl)(Cl)([Cl:27])=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21]3[C:20]4[CH:19]=[CH:18][CH:17]=[C:16]([CH3:22])[C:15]=4[N:14]=[C:13]([Cl:27])[C:12]=3[CH2:11][CH2:10]2)=[C:5]([CH3:24])[CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15749848HCID 15749848, compound

Product 1

HCID 15749850HCID 15749850, compound

Procedure

1-(4-methoxy-2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (1.0 g, 3.1 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 786 mg of desired compound as an oil in 75% 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-ca8cb5bdbdf54805a6030eb835da3197
Source dataset
uspto-grants-1999_06
Patent number
US05914402

Reaction notes

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