Phosphorus pentachloride → 4-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile
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
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
- customthe solid was collected
- dissolutionThe solid was dissolved in 700 ml ethyl acetate
- washwashed with cold dilute sodium hydroxide solution
- dry with materialThe solution was dried over magnesium sulfate
- 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-dfc3cc2b6ee04dfc9635b097a7f01d9b
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288082B1
Reaction notes
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