m-Chloroperbenzoic acid → 8-Acetamido-5-(m-acetoxybenzylsulfonyl)quinoline-N-oxide

HRID 904722Notes

Reaction equation

HRID 904722 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26](=[O:28])[CH3:27])[CH:20]=2)(=[O:17])=[O:16])=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:37])C=1>>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26](=[O:28])[CH3:27])[CH:20]=2)(=[O:17])=[O:16])=[C:9]2[C:14]=1[N+:13]([O-:37])=[CH:12][CH:11]=[CH:10]2)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 204311103-[(8-Acetamidoquinoline-5-sulfonyl)methyl]phenyl acetate

Product 1

HCID 204311098-Acetamido-5-(m-acetoxybenzylsulfonyl)quinoline-N-oxide

Procedure

8-Acetamido-5-(m-acetoxybenzylsulfonyl)quinoline (3.98 g, 10 mmole) was dissolved in 30 ml of dichlomethane and treated with m-chloroperbenzoic acid (2.03 g). The solution was stirred for 3 days at room temperature. Some m-chlorobenzoic acid which separated was filtered off and the filtrate concentrated to a syrup. On boiling with 40 ml 2-propanol a pale yellow solid was induced to crystallize. After chilling in an ice bath, the solid was filtered off, washed with 2-propanol and ether, and dried to yield 3.8 g (92 percent). The structure was confirmed by NMR.

Workup

  1. customSome m-chlorobenzoic acid which separated
  2. filtrationwas filtered off
  3. concentrationthe filtrate concentrated to a syrup
  4. customto crystallize
  5. temperatureAfter chilling in an ice bath
  6. filtrationthe solid was filtered off
  7. washwashed with 2-propanol and ether
  8. customdried
  9. customto yield 3.8 g (92 percent)

Sources & evidence

ORD record
ord-8f6f1f584cce40ebb0fe4caf61712fc9
Source dataset
uspto-grants-1983_12
Patent number
US04419435

Reaction notes

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