Thionyl Chloride → 4-Chloro-7-fluoroquinoline-3-carbonitrile
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>CN(C)C=O>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[C:12]#[N:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 7-fluoro-4-hydroxyquinoline-3-carbonitrile (2.02 g, 10.7 mmol) and a few drops of N, N-dimethylformamide in 16.0 mL of thionyl chloride is heated at reflux for 1.5 h. The reaction mixture was concentrated in vacuo and toluene (20 mL) is added and the mixture is again concentrated in vacuo to provide 2.18 g of 4-chloro-7-fluoroquinoline-3-carbonitrile as a yellow solid, mp 163-165° C.
Workup
- temperatureis heated
- temperatureat reflux for 1.5 h
- concentrationThe reaction mixture was concentrated in vacuo and toluene (20 mL)
- additionis added
- concentrationthe mixture is again concentrated in vacuo
Sources & evidence
- ORD record
- ord-674890530a6e46b996d9f71949040f65
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780996B2
Reaction notes
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