Nitric Acid → Nitro-oxazine

HRID 2178143Notes

Reaction equation

HRID 2178143 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].[OH-].[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 14798Sodium HydroxideHCID 12313776Oxazine

Product 1

HCID 66992931Nitro-oxazine

Conditions

Temperature
0 °C

Procedure

To concentrated sulfuric acid (13 ml) was added portionwise the oxazine IX (3.0 mmol) at 22° C., the solution obtained was cooled to 0° C. and treated with red fuming HNO3 (0.19 ml) over 20 min and stirring was continued at 0° C. for 1 h. The reaction mixture was slowly added to crushed ice (60 g), the pH was adjusted to 10 using NaOH, the aqueous layer was extracted with AcOEt, the organic layer was dried, evaporated and the residue was chromatographed on silica gel using a mixture of heptane/AcOEt 3:1 to afford the pure nitro-oxazine X.

Workup

  1. customthe solution obtained
  2. additionThe reaction mixture was slowly added
  3. extractionthe aqueous layer was extracted with AcOEt
  4. customthe organic layer was dried
  5. customevaporated
  6. customthe residue was chromatographed on silica gel using
  7. additiona mixture of heptane/AcOEt 3:1

Sources & evidence

ORD record
ord-55a86c2b9d394db6a15f642eae29349f
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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