Phosphorus oxychloride → HCID 11129151, compound

HRID 548448Notes

Reaction equation

HRID 548448 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N+:16]([O-:18])=[O:17])[CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]#[N:14])=[C:8]2O.P(Cl)(Cl)(Cl)(Cl)[Cl:20].P(Cl)(Cl)(Cl)=O>CCCCCC>[Cl:20][C:8]1[C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([N+:16]([O-:18])=[O:17])[CH:6]=2)[N:11]=[CH:10][C:9]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178493298HCID 178493298, compound

Product 1

HCID 11129151HCID 11129151, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 4 g (16 mmol) of 8-Methoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile, 6.66 g (32 mmol) of phosphorous pentachloride, and 15 ml of phosphorous oxychloride was refluxed for 2.5 hours. The mixture was diluted with hexane and the solid was collected. The solid was dissolved in 500 ml of ethyl acetate and washed with cold diluted sodium hydroxide solution. The solution was dried over magnesium sulfate and filtered through a pad of silica gel. The solvent was removed giving 2.05 g of tan solid: mass spectrum (electrospray, m/e) M+H 263.7.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customthe solid was collected
  3. dissolutionThe solid was dissolved in 500 ml of ethyl acetate
  4. washwashed with cold diluted sodium hydroxide solution
  5. dry with materialThe solution was dried over magnesium sulfate
  6. filtrationfiltered through a pad of silica gel
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-3fb63373fe634f4a9f0a042e964c4506
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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