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

HRID 1934895Notes

Reaction equation

HRID 1934895 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-3-quinolinecarbonitrile 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-3-quinolinecarbonitrile 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-3-quinolinecarbonitrile as a tan solid

Sources & evidence

ORD record
ord-5802496072b14831ae3a0d98c4690b5f
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

Loading…