m-Chloroperbenzoic acid → 1-[8-(Benzyloxy)-1-oxo-1lambda~5~-quinolin-5-yl]ethan-1-one

HRID 883627Notes

Reaction equation

HRID 883627 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)(=[O:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:27]>ClCCl>[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N+:9]2[O-:27])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 137448911-[8-(Benzyloxy)quinolin-5-yl]ethan-1-one

Product 1

HCID 137448921-[8-(Benzyloxy)-1-oxo-1lambda~5~-quinolin-5-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

5-Acetyl-8-benzyloxyquinoline (200 gms/0.72 moles) was dissolved in dichloromethane (4 liters) at room temperature. To this solution was added m-chloroperoxybenzoic acid (355.64 gms/1.44 moles) in 90 minutes under stiffing. The mixture was stirred at 25-30° C. for 2 hours. After completion of reaction, reaction mass was quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes and stirred for 5-10 minutes at same temperature. The organic layer was separated and aqueous layer was extracted with dichloromethane (2.5 liters). The organic layers were combined and washed with brine solution (2.5 liters). The dichloromethane was distilled out under vacuum at 40° C. The residue was stripped with acetone (500 ml) to remove traces of dichloromethane. The residue was stirred with acetone (200 ml) and chilled to 0-5° C. for 2 hours. The resulting 5-Acetyl-8-benzyloxyquinoline-N-oxide was isolated by filtration and washed with diethyl ether (200 ml), dried under vacuum at 60-65° C. for 2-3 hours. Yield-116 gms.

Workup

  1. customAfter completion of reaction, reaction mass
  2. customwas quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes
  3. stirringstirred for 5-10 minutes at same temperature
  4. customThe organic layer was separated
  5. extractionaqueous layer was extracted with dichloromethane (2.5 liters)
  6. washwashed with brine solution (2.5 liters)
  7. distillationThe dichloromethane was distilled out under vacuum at 40° C
  8. customto remove traces of dichloromethane
  9. stirringThe residue was stirred with acetone (200 ml)
  10. temperaturechilled to 0-5° C. for 2 hours

Sources & evidence

ORD record
ord-d415230ae7514430aa602df072d22cbb
Source dataset
uspto-grants-2012_08
Patent number
US08236959B2

Reaction notes

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