Thionyl Chloride → HCID 5007017, compound

HRID 986280Notes

Reaction equation

HRID 986280 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18](O)=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.S(Cl)(Cl)=O.[CH3:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH:28]([CH3:32])[NH:27]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]([N:27]2[CH:28]([CH3:32])[CH2:29][CH2:30][CH2:31][CH:26]2[CH3:25])=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 68843NanofinHCID 2691712-(2-chlorophenyl)quinoline-4-carboxylic acid

Product 1

HCID 5007017HCID 5007017, compound

Procedure

2-(2-Chlorophenyl)-quinoline-4-carboxylic acid (5.7 g) and thionyl chloride (15 ml) are heated under reflux for 1 hour. The thionyl chloride is evaporated off, the residue is taken up in toluene (40 ml) and the toluene is also evaporated off. Toluene (50 ml) is then added to the residue obtained, followed by the dropwise introduction of 2,6-dimethylpiperidine (6.78 g), with stirring. The mixture is stirred for 1 hour at ambient temperature, the precipitate is filtered off and the filtrate is evaporated under reduced pressure. The residue is taken up in water (50 ml) and chloroform (50 ml). The organic phase is decanted and the aqueous phase is extracted with chloroform (50 ml). The organic phases are combined, dried over magnesium sulphate and evaporated under reduced pressure.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe thionyl chloride is evaporated off
  3. customthe toluene is also evaporated off
  4. additionToluene (50 ml) is then added to the residue
  5. customobtained
  6. stirringThe mixture is stirred for 1 hour at ambient temperature
  7. filtrationthe precipitate is filtered off
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe organic phase is decanted
  10. extractionthe aqueous phase is extracted with chloroform (50 ml)
  11. dry with materialdried over magnesium sulphate
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-afd92509fc3e4e79ae28ad8e77046db8
Source dataset
uspto-grants-1987_12
Patent number
US04711890

Reaction notes

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