m-Chloroperbenzoic acid → HCID 53836303, compound

HRID 1073892Notes

Reaction equation

HRID 1073892 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:7][CH: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])[CH2:7][CH: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 19895656methyl 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carboxylate

Product 1

HCID 53836303HCID 53836303, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

313 mg of methyl 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carboxylate were dissolved in 10 ml of dichloromethane at room temperature and 283 mg of m-chloroperbenzoic acid were added. After stirring at room temperature for 2 hours the mixture was washed with sodium o bisulphite solution and sodium bicarbonate solution. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using initially 2% (v/v) methanol/ethyl acetate and finally 5% (v/v) methanol/ethyl acetate for the elution. There were obtained 250 mg of 2-[3,4-dihydro-6-(methoxycarbonyl)-2,2-dimethyl-2H-1-benzopyran-4-yl]pyridine N-oxide as an oil which solidified upon trituration with diethyl ether. After recrystallization from toluene the product melted at 128-130° C.

Workup

  1. washwas washed with sodium o bisulphite solution and sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel using initially 2% (v/v) methanol/ethyl acetate and finally 5% (v/v) methanol/ethyl acetate for the elution

Sources & evidence

ORD record
ord-9588a37231104529af167c1ac0c5c4c8
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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