m-Chloroperbenzoic acid → HCID 53978841, compound

HRID 892514Notes

Reaction equation

HRID 892514 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:4]=2[O:3]1.ClC1C=CC=C(C(OO)=[O:31])C=1>ClCCl>[CH3:1][C:2]1([CH3:22])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:31])[C:5]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895665HCID 19895665, compound

Product 1

HCID 53978841HCID 53978841, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

248 mg of 3.4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-6-nitro-2H-1-benzopyran were dissolved in 20 ml of dichloromethane at room temperature and 222 mg of m-chloroperbenzoic acid were added. After stirring at room temperature overnight the solution was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water. The organic phase was dried over sodium sulphate and evaporated. The resulting solid was triturated with diethyl ether, filtered off and recrystallized from acetonitrile to give 133 mg of 2-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1-benzopyran-4-yl)-3-methylpyridine N-oxide of melting point 218°-220° C.

Workup

  1. washwas washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe resulting solid was triturated with diethyl ether
  5. filtrationfiltered off
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-7f37d2a9b50d42f98a304021cad0d524
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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