Nitric Acid → HCID 57437664, compound

HRID 924580Notes

Reaction equation

HRID 924580 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH:4]=[C:5]([CH3:7])[N:6]=1.[N+:16]([O-])([OH:18])=[O:17].C(=O)(O)[O-].[Na+]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH3:1][C:2]1[N:3]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[C:4]([N+:16]([O-:18])=[O:17])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 57437662HCID 57437662, compound

Product 1

HCID 57437664HCID 57437664, compound

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Conditions

Temperature
0 °C

Procedure

Compound 6 (6.82 grams, 34.5 mmol) was added in portions to trifluoroacetic anhydride (50 mL) cooled to 0° C. After 15 minutes the sodium chloride ice water bath was replaced with a dry ice acetone bath and nitric acid (6.0 mL 70%) was added drop wise. This was stirred to ambient temperature for 16 hours after which time it was pored into ice-water and neutralized with solid sodium bicarbonate. The product was extracted with dichloromethane and purified on a silica gel flash column eluted with 49:1 dichloromethane-methanol to give the desired product as an orange paste. LCMS data supported the structure.

Workup

  1. extractionThe product was extracted with dichloromethane
  2. custompurified on a silica gel flash column
  3. washeluted with 49:1 dichloromethane-methanol

Sources & evidence

ORD record
ord-9ee4d26e7d234725940874d79c6d6ce3
Source dataset
uspto-grants-2016_03
Patent number
US09281483B2

Reaction notes

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