m-Chloroperbenzoic acid → 2-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)methylpyridine N-oxide

HRID 37113Notes

Reaction equation

HRID 37113 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=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>C(Cl)Cl.C(=O)([O-])O.[Na+]>[CH3:1][C:2]1([CH3:22])[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=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

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 105902573,4-dihydro-2,2-dimethyl-6-nitro-4-(2-pyridylmethyl)-2H-1,4-benzoxazine

Product 1

HCID 108291282-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)methylpyridine N-oxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In 4 ml of methylene chloride was dissolved 0.33 g of 3,4-dihydro-2,2-dimethyl-6-nitro-4-(2-pyridylmethyl)-2H-1,4-benzoxazine followed by addition of 0.26 g of m-chloroperbenzoic acid, and the mixture was stirred at room temperature overnight. This reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give crude crystals of 2-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)methylpyridine N-oxide. Recrystallization from ethanol-chloroform gave 0.2 g of the object compound. This compound was found to have the following physicochemical properties.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-79e3860a41d84992b0eaba48321c71fb
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

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