Dimethylformamide → HCID 22646521, compound

HRID 393585Notes

Reaction equation

HRID 393585 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[NH:9][CH:8]=[CH:7][C:6]2=O)#[N:2].CN(C=O)C.S(Cl)([Cl:26])=O>>[ClH:26].[Cl:26][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([C:1]#[N:2])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22646530HCID 22646530, compound

Product 1

HCID 22646521HCID 22646521, compoundYield 82%

Procedure

6-Cyano-7-(2-methoxyethoxy)-1,4-dihydroquinolin-4-one (1.9 g, 7.8 mmol) and DMF (0.2 ml) in thionyl chloride (50 ml) were heated at reflux for 2 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene and dried under vacuum to give 4-chloro-6-cyano-7-(2-methoxyethoxy)quinoline hydrochloride (2.4 g, 82%) as a solid.

Workup

  1. temperatureat reflux for 2 hours
  2. customExcess thionyl chloride was removed by evaporation
  3. customthe residue azeotroped with toluene
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1dbead239fa9439db36383519d9cc2b1
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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