Water → HCID 59527026, compound

HRID 384431Notes

Reaction equation

HRID 384431 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]=[C:11]([CH3:20])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1.[OH-].[Na+].O>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N+:12]([O-:30])=[C:11]([CH3:20])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 59527169HCID 59527169, compound

Product 1

HCID 59527026HCID 59527026, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice-cold solution of 4-(benzyloxy)-2,3,6-trimethylquinoline (1.36 g) in chloroform (25 mL) was added m-chloroperbenzoic acid (75%, 1.35 g), and the mixture was stirred for 4.5 hours. A 1M aqueous sodium hydroxide solution (10 mL) and water (10 mL) were added to the reaction mixture, followed by extraction with chloroform (20 mL). The organic layer was washed sequentially with water and saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5) to obtain 4-(benzyloxy)-2,3,6-trimethylquinoline-1-oxide (1.20 g).

Workup

  1. extractionfollowed by extraction with chloroform (20 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-42b4d768ae254e609de8197825716e7c
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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