m-Chloroperbenzoic acid → HCID 53816727, compound

HRID 892554Notes

Reaction equation

HRID 892554 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]3[N:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[C:7]=2[CH:24]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N+:19]=3[O-:33])[C:7]=2[CH:24]=1)#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895585HCID 19895585, compound

Product 1

HCID 53816727HCID 53816727, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

237 mg of methyl 6-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-pyridinecarboxylate were dissolved in 30 ml of dichloromethane and 180 mg of m-chloroperbenzoic acid were added. The mixture was stirred at room temperature overnight and then washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. The resulting oil was triturated with diethyl ether to give a solid which was recrystallized from t-butyl methyl ether. There were obtained 60 mg of 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-(methoxycarbonyl)pyridine N-oxide of melting point 135°-137° C.

Workup

  1. washwashed in succession with sodium bisulphite solution, sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe resulting oil was triturated with diethyl ether
  5. customto give a solid which
  6. customwas recrystallized from t-butyl methyl ether

Sources & evidence

ORD record
ord-7775b7efc7e0481b9dabfeb4eb536653
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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