m-Chloroperbenzoic acid → Ro 31-6930

HRID 892516Notes

Reaction equation

HRID 892516 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:31])[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:16]2[CH:25]=[C:26]([C:29]#[N:30])[CH:27]=[CH:28][C:15]=2[O:14]1>ClCCl>[C:29]([C:26]1[CH:27]=[CH:28][C:15]2[O:14][C:13]([CH3:31])([CH3:12])[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N+:20]=3[O-:9])[C:16]=2[CH:25]=1)#[N:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 156813282,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 3036546Ro 31-6930Yield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

406 mg of m-chloroperbenzoic acid were added to a solution of 524 mg of 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile in 15 ml of dichloromethane at room temperature. After stirring at room temperature for 17 hours the solution was washed with sodium bicarbonate solution. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using methanol/ethyl acetate (1:4) for the elution. There were obtained 240 mg of 2-(6-cyano-2,2-dimethyl-2H1-benzopyran-4-yl)pyridine N-oxide of melting point 187°-189° C. after recrystallization from ethyl acetate.

Workup

  1. washwas washed with sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-4c10989c39af4541ad7b4121ec739140
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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