m-Chloroperbenzoic acid → HCID 54394870, compound

HRID 892551Notes

Reaction equation

HRID 892551 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:32])[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)[C:16]2[CH:26]=[C:27]([C:30]#[N:31])[CH:28]=[CH:29][C:15]=2[O:14]1>ClCCl>[C:30]([C:27]1[CH:28]=[CH:29][C:15]2[O:14][C:13]([CH3:32])([CH3:12])[CH:18]=[C:17]([C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N+:20]=3[O-:9])[C:16]=2[CH:26]=1)#[N:31]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895684HCID 19895684, compound

Product 1

HCID 54394870HCID 54394870, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

406 mg of m-chloroperbenzoic acid were added to a solution of 552 mg of 2,2-dimethyl-4-(4-methyl-2-pyridyl)-2H-1-benzopyran-6-carbonitrile in 20 ml of dichloromethane and the mixture was stirred for 1 hour. Subsequently, the mixture was washed with sodium bicarbonate solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using methanol/ethyl acetate (1:4) for the elution. After recrystallization from ethyl acetate there were obtained 140 mg of 2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)-4-methylpyridine N-oxide of melting point 199°-201° C.

Workup

  1. washSubsequently, the mixture was washed with sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-834236ab76b5431e9d1e209278b03da9
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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