Phosphorus pentachloride → 4-Chloro-7-methoxyquinoline-3-carbonitrile

HRID 1934892Notes

Reaction equation

HRID 1934892 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:17]>>[Cl:17][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=[CH:9][C:8]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 125594304-Hydroxy-7-methoxyquinoline-3-carbonitrile

Product 1

HCID 125594314-Chloro-7-methoxyquinoline-3-carbonitrile

Conditions

Temperature
165 °C

Procedure

A mixture of 4.0 g (20 mmol) of 1,4-dihydro-7-methoxy-4-oxo-3-quinolinecarbonitrile and 8.3 g (40 mmol) of phosphorous pentachloride was heated at 165° C. for 3 hours. The mixture was diluted with hexanes and the solid was collected. The solid was mixed with brine and dilute sodium hydroxide solution and extracted several times with a mixture of tetrahydrofuran and ethyl acetate. The solution was dried over magnesium sulfate and filtered through a pad of silica gel giving 3.7 g of 4-chloro-7-methoxy-3-quinolinecarbonitrile as a white solid: mass spectrum (electrospray, m/e): M+H 218.9.

Workup

  1. customthe solid was collected
  2. additionThe solid was mixed with brine and dilute sodium hydroxide solution
  3. extractionextracted several times
  4. additionwith a mixture of tetrahydrofuran and ethyl acetate
  5. dry with materialThe solution was dried over magnesium sulfate
  6. filtrationfiltered through a pad of silica gel giving 3.7 g of 4-chloro-7-methoxy-3-quinolinecarbonitrile as a white solid

Sources & evidence

ORD record
ord-c34f4981e9b34d008087acbb69c56c10
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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