Phosphorus oxychloride → 4-Chlorobenzo[g]quinoline-3-carbonitrile

HRID 2213715Notes

Reaction equation

HRID 2213715 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[NH:5][CH:4]=[C:3]1[C:16]#[N:17].P(Cl)(Cl)([Cl:20])=O>CN(C)C=O>[Cl:20][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 98344134-Oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Product 1

HCID 98346304-Chlorobenzo[g]quinoline-3-carbonitrileYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A reaction mixture of 3.5 g (16 mmol) of 4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile in 35 mL of phosphorus oxychloride and 22 drops of N,N-dimethylformamide (DMF) is heated at 100–110° C. for 5 hours. After cooling, the mixture is concentrated to dryness in vacuo to give a dark residue. The residue is partitioned between methylene chloride and ice-cooled saturated aqueous sodium carbonate solution. The organic layer is washed with ice-cooled brine and dried over sodium sulfate. The organic solvent is passed through a short column of silica gel, and further eluted with additional methylene chloride. Removal of the solvent yields 1.89 g (49.5%) of the product as a bright yellow solid, mp 253–255° C.

Workup

  1. temperatureis heated at 100–110° C. for 5 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated to dryness in vacuo
  4. customto give a dark residue
  5. customThe residue is partitioned between methylene chloride and ice-
  6. temperaturecooled saturated aqueous sodium carbonate solution
  7. washThe organic layer is washed with ice-
  8. temperaturecooled brine
  9. dry with materialdried over sodium sulfate
  10. washfurther eluted with additional methylene chloride
  11. customRemoval of the solvent

Sources & evidence

ORD record
ord-8298d1868b904d48ab9dc49d0e6c4ece
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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