m-Chloroperbenzoic acid → Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 1-oxide

HRID 964575Notes

Reaction equation

HRID 964575 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:30][Cl:31])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[CH:13][C:12]([O:26][CH3:27])=[C:11]([O:28][CH3:29])[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[C:7]([CH2:30][Cl:31])=[N+:8]([O-:40])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[CH:13][C:12]([O:26][CH3:27])=[C:11]([O:28][CH3:29])[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 21851158Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 1-oxideYield 65%

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-0237374de4fa4d2aa83fcc1677516c25
Source dataset
uspto-grants-1998_06
Patent number
US05770602

Reaction notes

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