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

HRID 37109Notes

Reaction equation

HRID 37109 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][N:6]([N:8]=O)[C:5]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:4]=2[O:3]1.[OH-].[Na+]>CO.O>[NH2:8][N:6]1[C:5]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:4]=2[O:3][C:2]([CH3:17])([CH3:1])[CH2:7]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 152724143,4-dihydro-2,2-dimethyl-6-nitro-4-nitroso-2H-1,4-benzoxazine

Product 1

HCID 105610394-amino-3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazineYield 18.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 69 ml of methanol was dissolved 2.29 g of 3,4-dihydro-2,2-dimethyl-6-nitro-4-nitroso-2H-1,4-benzoxazine and the solution was cooled on an ice bath. After addition of a solution of 1.16 g of sodium hydroxide in 8.1 ml of water to the above solution, 3.13 g of formamidinosulfinic acid was gradually added. The mixture was stirred at room temperature overnight and, then, concentrated. The concentrate was subjected to column chromatography (eluent: hexane;ethyl acetate=9:1) to give 0.4 g of 4-amino-3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazine.

Workup

  1. temperaturethe solution was cooled on an ice bath
  2. additionwas gradually added
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b9aaa8b25caa44d99997355836e28cc8
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

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