m-Chloroperbenzoic acid → Ethyl 2-chloroquinoline-6-carboxylate

HRID 49927Notes

Reaction equation

HRID 49927 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:16]C1C=CC=C(C(OO)=O)C=1>ClCCl>[Cl:16][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=2)[N:1]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 946706-Quinolinecarboxylic acid, ethyl ester

Product 1

HCID 17834353Ethyl 2-chloroquinoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.8 g (29 mmol) of ethyl quinoline-6-carboxylate was stirred in 80 ml of dichloromethane. 6.2 g of m-chloroperbenzoic acid was added to the obtained mixture under cooling with ice, and they were stirred at room temperature overnight. The mixture was washed with 10% aqueous sodium sulfite solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. 70 ml of dichloromethane and 35 ml of phosphoryl chloride were added to the residue, and they were stirred at 50° C. overnight. The solvent was evaporated, and the residue was treated with dichloromethane as the extracting solvent by an ordinary method. After the purification by the silica gel chromatography (ethyl acetate/hexane), the title compound was obtained.

Workup

  1. temperatureunder cooling with ice, and they
  2. washThe mixture was washed with 10% aqueous sodium sulfite solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. addition70 ml of dichloromethane and 35 ml of phosphoryl chloride were added to the residue, and they
  6. stirringwere stirred at 50° C. overnight
  7. customThe solvent was evaporated
  8. additionthe residue was treated with dichloromethane as the extracting solvent by an ordinary method
  9. customAfter the purification by the silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b6a3a3359824e80b3b2fc91bfde6b5c
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Reaction notes

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