m-Chloroperbenzoic acid → HCID 54331976, compound

HRID 1073972Notes

Reaction equation

HRID 1073972 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:31])[CH2:18][CH:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=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])[CH2:18][CH:17]([C:19]3[CH:20]=[N+:21]([O-:9])[CH:22]=[CH:23][CH:24]=3)[C:16]=2[CH:25]=1)#[N:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895626HCID 19895626, compound

Product 1

HCID 54331976HCID 54331976, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

610 mg of m-chloroperbenzoic acid were added to a solution of 792 mg of 3,4-dihydro-2,2-dimethyl-4-(3-pyridyl)-2H-1-benzopyran-6-carbonitrile in 15 ml of dichloromethane. After stirring at room temperature for one hour the mixture was washed with sodium bisulphite solution and sodium bicarbonate solution. The organic phase was dried over sodium sulphate and evaporated. The residue was crystallized from t-butyl methyl ether to give 710 mg of 3-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide in the form of a solid of melting point 134°-137° C.

Workup

  1. washwas washed with sodium bisulphite solution and sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was crystallized from t-butyl methyl ether

Sources & evidence

ORD record
ord-ff86e7b253534141aeef5d0d9d7c9136
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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