Thionyl Chloride → 4-Chloro-7-fluoroquinoline-3-carbonitrile

HRID 1837348Notes

Reaction equation

HRID 1837348 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

HCID 24386Thionyl ChlorideHCID 1785103157-Fluoro-4-hydroxyquinoline-3-carbonitrile

Product 1

HCID 234980814-Chloro-7-fluoroquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

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

  1. temperatureis heated
  2. temperatureat reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo and toluene (20 mL)
  4. additionis added
  5. 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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