m-Chloroperbenzoic acid → HCID 86092313, compound

HRID 1584141Notes

Reaction equation

HRID 1584141 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](CCl)=[N:8][C:9]2[C:14]([C:15]=1C1C=CC(OC)=C(OC)C=1)=[CH:13][C:12](OC)=[C:11](OC)[CH:10]=2)=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=[O:40])C=1>CO>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N+:8]([O-:40])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Product 1

HCID 86092313HCID 86092313, compoundYield 136.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylic acid ethyl ester (3.0 g), m-chloroperbenzoic acid (85%, 2.3 g) and methanol (40 ml) was stirred under refluxing conditions for 2 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was poured over chloroform. The chloroform layer was washed with water and dried (MgSO4), after which the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (6:4, v/v) to yield 2-chloromethyl-6,7-dimethoxy-4-3,4-dimethoxyphenyl)quinoline-3-carboxylic acid ethyl ester 1-oxide (2.0 g, 65%), which was then recrystallized from acetone-isopropyl ether to yield a colorless prismatic crystal having a melting point of 193 to 194° C.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. additionThe residue was poured over chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationafter which the solvent was distilled off under reduced pressure
  7. washeluted with chloroform-ethyl acetate (6:4, v/v)

Sources & evidence

ORD record
ord-72f28380730f4fd194464b7024b51d7c
Source dataset
uspto-grants-1999_08
Patent number
US05932592

Reaction notes

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