Phosphorus oxychloride → 4-Chloro-7-ethoxy-6-nitroquinoline-3-carbonitrile

HRID 548446Notes

Reaction equation

HRID 548446 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](O)=[C:9]([C:14]#[N:15])[CH:10]=[N:11]2)=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:21].P(Cl)(Cl)(Cl)=O>CCCCCC>[Cl:21][C:8]1[C:7]2[C:12](=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([N+:17]([O-:19])=[O:18])[CH:6]=2)[N:11]=[CH:10][C:9]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178465845HCID 178465845, compound

Product 1

HCID 110113054-Chloro-7-ethoxy-6-nitroquinoline-3-carbonitrileYield 58.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 3.45 g (13 mmol) of 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile, 5.55 g (26 mmol) of phosphorous pentachloride, and 10 ml of phosphorous oxychloride was refluxed for 3 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 2.1 g of beige solid: mass spectrum (electrospray, m/e) M+H 277.7.

Workup

  1. temperaturewas refluxed for 3 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-63a00747f41342b48bcb80504cfcf108
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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