m-Chloroperbenzoic acid → HCID 9828701, compound

HRID 617219Notes

Reaction equation

HRID 617219 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[C:19]([CH2:26][S:27][C:28]1[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=1)[C:18]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:17]2[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([O:47][CH3:48])[CH:40]=1>ClCCl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[C:19]([CH2:26][S:27]([C:28]1[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=1)=[O:6])[C:18]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:17]2[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([O:47][CH3:48])[CH:40]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10768373HCID 10768373, compound

Product 1

HCID 9828701HCID 9828701, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (85%, 830 mg) was added in small portions under ice-cooling to a solution of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[(1-methylimidazol- 2-yl)thiomethyl]quinoline-3-carboxylate (3.0 g) in dichloromethane (75 ml). The reaction mixture was stirred at room temperature for 2.5 hours, washed successively with 5% NaHSO3 aqueous solution, saturated aqueous solution of sodium bicarbonate and water, and dried (MgSO4). The solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate/methanol (10:1, v/v), ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2- [(1-methylimidazol-2-yl)sulfinylmethyl]quinoline-3-carboxylate (1.8 g, 58%) was obtained and recrystallized from acetone-ethyl ether.

Workup

  1. washwashed successively with 5% NaHSO3 aqueous solution, saturated aqueous solution of sodium bicarbonate and water
  2. dry with materialdried (MgSO4)
  3. distillationThe solvent was distilled off under reduced pressure
  4. washFrom the fraction eluted with ethyl acetate/methanol (10:1

Sources & evidence

ORD record
ord-c957cc16aa4f4303927c9192ff0ec544
Source dataset
uspto-grants-1999_09
Patent number
US05948782

Reaction notes

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