Sodium Hydroxide → 3,4-dihydro-2,2-dimethyl-6-nitro-4-nitroso-2H-1,4-benzoxazine

HRID 37108Notes

Reaction equation

HRID 37108 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][NH:6][C:5]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1.[N:16]([O-])=[O:17].[Na+].[OH-].[Na+]>CO.C(O)(=O)C.O>[CH3:1][C:2]1([CH3:15])[CH2:7][N:6]([N:16]=[O:17])[C:5]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 107270572,2-Dimethyl-6-nitro-3,4-dihydro-2H-benzo[B][1,4]oxazineHCID 23668193Sodium Nitrite

Product 1

HCID 152724143,4-dihydro-2,2-dimethyl-6-nitro-4-nitroso-2H-1,4-benzoxazineYield 93.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a mixture of 34 ml of methanol and 2.07 ml of acetic acid was dissolved 3 g of 3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazine. Then, a solution of 2.0 g of sodium nitrite in 6.6 ml of water was added dropwise and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with aqueous sodium hydroxide solution, concentrated under reduced pressure and extracted with chloroform. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 3.2 g of 3,4-dihydro-2,2-dimethyl-6-nitro-4-nitroso-2H-1,4-benzoxazine.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b2972482fd3342238ef85cf460a0b4a6
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

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