m-Chloroperbenzoic acid → HCID 54230993, compound

HRID 892528Notes

Reaction equation

HRID 892528 reaction equation
[CH3:1][C:2]1([CH3:22])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=[CH:17][C:4]=2[O:3]1.ClC1C=CC=C(C(OO)=[O:31])C=1>ClCCl>[CH3:21][O:20][C:18]([C:15]1[CH:16]=[CH:17][C:4]2[O:3][C:2]([CH3:22])([CH3:1])[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=3[O-:31])[C:5]=2[CH:14]=1)=[O:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895641HCID 19895641, compound

Product 1

HCID 54230993HCID 54230993, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

402 mg of methyl 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carboxylate were dissolved in 15 ml of dichloromethane at room temperature and 330 mg of m-chloroperbenzoic acid were added. After stirring at room temperature overnight the mixture was washed with sodium bisulphite solution and sodium bicarbonate solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 10% (v/v) methanol/ethyl acetate for the elution. The product was recrystallized from t-butyl methyl ether to give 65 mg of 2-[6-(methoxycarbonyl)-2,2-dimethyl-2H-1-benzopyran-4-yl]pyridine N-oxide of melting point 155°-157° C.

Workup

  1. washwas washed with sodium bisulphite solution and sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel using 10% (v/v) methanol/ethyl acetate for the elution
  5. customThe product was recrystallized from t-butyl methyl ether

Sources & evidence

ORD record
ord-6cec560e70e54d9d9a67a4ad9ef4648b
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

Loading…