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

HRID 1935053Notes

Reaction equation

HRID 1935053 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-4e60f7caa02047cd87a80a2843768946
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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