m-Chloroperbenzoic acid → HCID 17979838, compound

HRID 133098Notes

Reaction equation

HRID 133098 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[CH:16]2>ClCCl>[CH3:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N+:19]([O-:9])=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[CH:16]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5305631HCID 5305631, compound2×

Product 1

HCID 17979838HCID 17979838, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 46 g of m-chloroperbenzoic acid in 19 ml of dichloromethane is added dropwise to a solution of 17.6 g of 6-methyl-3-nitroquinoline (compound E2) in 400 ml of dichloromethane. The reaction mixture is stirred for 70 h, diluted with 20 ml of dichloromethane and extracted two times each with 800 ml of halfsaturated aqueous sodium hydrogencarbonate solution. The organic layer is dried over magnesium sulfate, filtered and evaporated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 98:2). 8.25 g of the title compound are obtained as yellow crystals.

Workup

  1. extractionextracted two times each with 800 ml of halfsaturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue is chromatographed on silica gel (dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-422e31590f1343149e9dc4436ca189c3
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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