Chlorine monoxide → 4-Chloro-8-methoxyquinoline-3-carbonitrile

HRID 612181Notes

Reaction equation

HRID 612181 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][CH:10]=[C:9]([C:13]#[N:14])[C:8]2=O.O(Cl)[Cl:17]>CN(C=O)C>[Cl:17][C:8]1[C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[N:11]=[CH:10][C:9]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 24646Chlorine monoxideHCID 22466766HCID 22466766, compound

Product 1

HCID 224666994-Chloro-8-methoxyquinoline-3-carbonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 3.8 g (19 mmol) of 1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarbonitrile and 40 mL of phosphorous oxochloride and 5 drops of DMF was refluxed for 0.5 hours. The mixture was evaporated to dryness and diluted with hexanes. The solid was collected and mixed with cold dilute sodium carbonate solution and extracted several times with ethyl acetate. The organic layer was dried over sodium sulfate and filtered through a pad of silica gel. Removal of the solvent gave 3.8 g of 4-chloro-8-methoxy-3-quinolinecarbonitrile as an off white solid in 91% yield, mass spectrum (electrospray, m/e): M+H 219.1.

Workup

  1. temperaturewas refluxed for 0.5 hours
  2. customThe mixture was evaporated to dryness
  3. additiondiluted with hexanes
  4. customThe solid was collected
  5. additionmixed with cold dilute sodium carbonate solution
  6. extractionextracted several times with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered through a pad of silica gel
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-842fc124540245e6a9afd36f97274121
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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