Dimethylformamide → Ethyl 6-chloro-2-methylquinoline-3-carboxylate

HRID 2187666Notes

Reaction equation

HRID 2187666 reaction equation
[CH3:1]N(C=O)C.P(Cl)(Cl)(Cl)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([CH3:26])=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:13]=1>ClCCCl>[Cl:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][CH:17]=1)[N:18]=[C:19]([CH3:26])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:1]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 38739ethyl 3-(4-chloroanilino)but-2-enoate

Product 1

HCID 11288138Ethyl 6-chloro-2-methylquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 6.2 g (83 mmol) DMF in 50 ml of 1,2 dichloroethane was carefully added 19.1 g (126 mmol) of phosphoryl chloride. After stirring for 10 min at ambient temperature a solution of 20 g (83 mol) of ethyl 3-(4-chlorophenylamino)but-2-enoate in 50 ml of 1,2 dichloroethane was added slowly, while the mixture turned dark in an exothermic reaction. Stirring at ambient temperature was continued for another hour followed by heating with reflux for 6 h. The mixture was poured on to crushed ice, washed twice with water, dried over sodium sulfate, and concentrated under reduced pressure. The title ester was obtained from the residue via flash chromatography on silica gel with dichloromethane/hexane 4:1.

Workup

  1. additionwas added slowly, while the mixture
  2. customturned dark in an exothermic reaction
  3. waitwas continued for another hour
  4. temperatureby heating
  5. temperaturewith reflux for 6 h
  6. additionThe mixture was poured on
  7. customto crushed ice
  8. washwashed twice with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-791b847c980d42218141872d67865483
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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