Nitric Acid → HCID 68194434, compound

HRID 2370651Notes

Reaction equation

HRID 2370651 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)[CH3:2].FC(F)(F)C(O)=O.[N+:22]([O-])([OH:24])=[O:23].N.O>>[CH2:13]([N:3]([CH2:1][CH3:2])[CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:22]([O-:24])=[O:23])[CH:10]=2)[CH2:5]1)[CH3:14]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 12896473Azane;hydrateHCID 44377347HCID 44377347, compound

Product 1

HCID 68194434HCID 68194434, compound

Conditions

Temperature
7.5 °C

Procedure

To a solution of Example 226A (2.0 g, 10.57 mmol) in trifluoroacetic acid (80 ml, 1038 mmol) was added nitric acid (0.726 ml, 10.57 mmol) dropwise at 0° C. The mixture was stirred at 0-15° C. for 5 hours. The solution was poured into ice/water (20 mL) and the pH was adjusted to 10 with NH3/H2O. The mixture was extracted with methylene chloride (4×50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to provide the title compound.

Workup

  1. extractionThe mixture was extracted with methylene chloride (4×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e85a0b596f4e49eb8565bf4e52dbaf88
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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