Nitric Acid → Nitro-oxazine

HRID 444801Notes

Reaction equation

HRID 444801 reaction equation
S(=O)(=O)(O)O.[O:6]1[CH:11]=[CH:10][CH:9]=[CH:8][NH:7]1.[N+:12]([O-])([OH:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>>[N+:12]([C:8]1[NH:7][O:6][CH:11]=[CH:10][CH:9]=1)([O-:14])=[O:13]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 12313776Oxazine

Product 1

HCID 66992931Nitro-oxazine

Conditions

Temperature
0 °C

Procedure

To concentrated sulfuric acid (2 ml) was added portion wise the oxazine XI (0.1 mmol) at 22° C., the solution obtained was cooled to 0° C. and treated with red fuming nitric acid (HNO3) (0.058 ml) and stiffing was continued at 0° C. for 2 h. The reaction mixture was slowly added to crushed ice, the pH was adjusted to 10 using a saturated sodium carbonate solution, the aqueous layer was extracted with AcOEt, the organic layer was dried and evaporated to afford the pure nitro-oxazine XII.

Workup

  1. customthe solution obtained
  2. additionThe reaction mixture was slowly added
  3. customto crushed ice
  4. extractionthe aqueous layer was extracted with AcOEt
  5. customthe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-fcfb178d65494208b3f7fc1c6ce5d085
Source dataset
uspto-grants-2013_07
Patent number
US08476264B2

Reaction notes

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