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

HRID 1380142Notes

Reaction equation

HRID 1380142 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=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl>[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-:30])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 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 6212ChloroformSolvent2×

Procedure

5 g of 5-acetyl-8-benzyloxyquinoline are dissolved in 50 ml of chloroform. The solution is ice-cooled and 3.12 g of 80% m-chloroperbenzoic acid are added thereto under stirring. The mixture is stirred at room temperature for 24 hours and at 50° C. for 7.5 hours. The mixture is then stirred at room temperature for 64 hours. 2 g of 80% m-chloroperbenzoic acid are further added to the mixture during the reaction. After the reaction, chloroform is added to the mixture. The mixture is washed with water, a 4% sodium bicarbonate solution and a saturated sodium chloride solution, dried and then evaporated under reduced pressure to remove chloroform. 5-Acetyl-8-benzyloxyquinoline-N-oxide is obtained as yellow solid.

Workup

  1. temperaturecooled
  2. stirringThe mixture is stirred at room temperature for 24 hours and at 50° C. for 7.5 hours
  3. stirringThe mixture is then stirred at room temperature for 64 hours
  4. additionis added to the mixture
  5. washThe mixture is washed with water
  6. dry with materiala 4% sodium bicarbonate solution and a saturated sodium chloride solution, dried
  7. customevaporated under reduced pressure
  8. customto remove chloroform

Sources & evidence

ORD record
ord-84885a0a360549c1adda6e6a0038d745
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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