Bicarbonate Ion → HCID 10755399, compound

HRID 326585Notes

Reaction equation

HRID 326585 reaction equation
[CH3:1][C:2]1([CH3:18])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3]1.S(=O)(=O)(O)O.[N+:24]([O-])([OH:26])=[O:25].[OH-].[Na+].C(=O)(O)[O-]>C(O)(=O)C>[N+:24]([C:15]1[CH:16]=[CH:17][C:4]2[O:3][C:2]([CH3:18])([CH3:1])[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:5]=2[CH:14]=1)([O-:26])=[O:25]

Participants

7

Reactant 5

HCID 769Bicarbonate IonHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 10752413HCID 10752413, compound

Product 1

HCID 10755399HCID 10755399, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,2-Dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.50 g) was dissolved in acetic acid (1 ml) and to the solution was added conc. sulfuric acid (3 ml) with ice-cooling. Conc. nitric acid (0.2 ml) was then added to the mixture, and the mixture was stirred for 10 minutes with ice-cooling. The reaction mixture was added slowly to a thoroughly cooled mixture of an aqueous 5N sodium hydroxide solution (50 ml) and saturated bicarbonate solution (20 ml) to quench the reaction. The mixture was extracted by addition of ethyl acetate. The mixture was successively washed with an aqueous sodium bicarbonate solution and saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from hexane to obtain 6-nitro-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.58 g) (Compound 11).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customto quench
  4. customthe reaction
  5. extractionThe mixture was extracted by addition of ethyl acetate
  6. washThe mixture was successively washed with an aqueous sodium bicarbonate solution and saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-b62e1749aecf441ab6c150863a28237d
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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