Dimethylformamide → 4-Chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrile

HRID 1595730Notes

Reaction equation

HRID 1595730 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](O)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:18][CH3:19].C(Cl)(=O)C([Cl:23])=O.CN(C)C=O>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:23])=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178486762HCID 178486762, compound

Product 1

HCID 111092524-Chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrileYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8 g (28.7 mmol) of 7-(2-Chloro-ethoxy)-4-hydroxy-6-methoxy-quinoline-3-carbonitrile and 18.2 g (143.5 mmol) of oxalyl chloride in 80 ml of methylene chloride containing 0.26 g of dimethylformamide was stirred at reflux for 2.5 hr. The solvent was removed. The residue was mixed with cold dilute sodium hydroxide and extracted several time with ethyl acetate and tetrahydrofuran. The combined extracts were dried over magnesium sulfate and the solution was passed through a short silica gel column. The solvents were removed giving 6.0 g of the title compound as an off-white solid that is used without additional purification.

Workup

  1. temperatureat reflux for 2.5 hr
  2. customThe solvent was removed
  3. additionThe residue was mixed with cold dilute sodium hydroxide
  4. extractionextracted several time with ethyl acetate and tetrahydrofuran
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customThe solvents were removed

Sources & evidence

ORD record
ord-50bc5d15ed2945138bbf67748370084b
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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