Phosphorus oxychloride → HCID 17979843, compound

HRID 133097Notes

Reaction equation

HRID 133097 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([O-])=[CH:8][C:7]([N+:14]([O-:16])=[O:15])=[CH:6]2.P(Cl)(Cl)([Cl:19])=O>ClCCl>[Cl:19][C:8]1[C:7]([N+:14]([O-:16])=[O:15])=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 17979841HCID 17979841, compound2×

Product 1

HCID 17979843HCID 17979843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 8.0 g of 6-methoxy-3-nitroquinoline-1-oxide (compound D3) in 80 ml of phosphorus oxychloride is stirred at 100° C. for 30 min. After cooling to room temperature, the reaction mixture is added to 500 ml of ice water, diluted with 250 ml of dichloromethane and extracted three times each with 250 ml of a halfsaturated aqueous potassium carbonate solution. The organic layer is dried using magnesium sulfate, filtered and evaporated in vacuo. The residue is recrystallized from diethylether to give 5.6 g of the title compound as violet solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted three times each with 250 ml of a halfsaturated aqueous potassium carbonate solution
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue is recrystallized from diethylether

Sources & evidence

ORD record
ord-2e36ad49b364487d9fb81edf6c25489f
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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