Phosphorus oxychloride → 4-Chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

HRID 2213720Notes

Reaction equation

HRID 2213720 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:20][CH3:21])=[CH:5][C:6]2[CH:15]=[C:14]3[C:9]([C:10](=O)[C:11]([C:16]#[N:17])=[CH:12][NH:13]3)=[CH:8][C:7]=2[CH:19]=1.P(Cl)(Cl)([Cl:24])=O>CN(C=O)C>[Cl:24][C:10]1[C:9]2[C:14](=[CH:15][C:6]3[CH:5]=[C:4]([O:20][CH3:21])[C:3]([O:2][CH3:1])=[CH:19][C:7]=3[CH:8]=2)[N:13]=[CH:12][C:11]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 99435817,8-Dimethoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Product 1

HCID 99441164-Chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrileYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 356.2 mg (1.3 mmol) of 7,8-dimethoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile in 5 mL of phosphorus oxychloride and 4 drops of DMF is heated at 100–110° C. for 4.5 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 cooled brine and dried over sodium sulfate. The organic solvent is passed through a short column of silica gel, and the column is first eluted with additional methylene chloride, then a 99:1 methylene chloride/ethyl acetate solution. Removal of the solvent yields 187.0 mg (49.4%) of the product as a bright yellow solid, mp>265° C.

Workup

  1. temperatureis heated at 100–110° C. for 4.5 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 cooled brine
  8. dry with materialdried over sodium sulfate
  9. washthe column is first eluted with additional methylene chloride
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-613427e194fd4232a0c97ef0897e3ad6
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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