Phosphorus pentachloride → 4-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

HRID 548407Notes

Reaction equation

HRID 548407 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][C:4]=1[N+:16]([O-:18])=[O:17].P(Cl)(Cl)(Cl)(Cl)[Cl:20]>>[Cl:20][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([N+:16]([O-:18])=[O:17])[CH:5]=2)[N:10]=[CH:9][C:8]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 109777094-Hydroxy-7-methoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

Conditions

Temperature
165 °C

Procedure

A mixture of 5.3 g (21.6 mmol) of 1,4-dihydro-7-methoxy-6-nitro-4-oxo-quinoline-3-carbonitrile and 9 g (43.2 mmol) of phosphorous pentachloride was heated at 165° C. for 2 hours. The mixture was diluted with hexanes and the solid was collected. The solid was dissolved in 700 ml ethyl acetate and washed with cold dilute sodium hydroxide solution. The solution was dried over magnesium sulfate and filtered through a pad of silica gel giving 5.2 g of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile as a tan solid.

Workup

  1. customthe solid was collected
  2. dissolutionThe solid was dissolved in 700 ml ethyl acetate
  3. washwashed with cold dilute sodium hydroxide solution
  4. dry with materialThe solution was dried over magnesium sulfate
  5. filtrationfiltered through a pad of silica gel giving 5.2 g of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile as a tan solid

Sources & evidence

ORD record
ord-6b70be1f8dcf45f6957f6e36845f091c
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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