Nitric Acid → HCID 18470694, compound

HRID 2228621Notes

Reaction equation

HRID 2228621 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[C:12]([C:15]1[C:19]([CH3:20])=[C:18]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[NH:17][CH:16]=1)(=[O:14])[CH3:13].C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[C:12]([C:15]1[C:19]([CH3:20])=[C:18]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[NH:17][C:16]=1[N+:8]([O-:11])=[O:9])(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 11412986HCID 11412986, compound

Product 1

HCID 18470694HCID 18470694, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a cooled (−10˜−20° C.) acetic anhydride (1.2 mL) was added fuming nitric acid (0.13 mL) and sulfuric acid (1 drop). After stirring for 3 minutes, 3-acetyl-4-methyl-5-(4-pyridyl)-1H-pyrrole (0.2 g, 1 mmol) was added to the mixture. The resulting mixture was allowed to warm to room temperature and stirred for additional 1 hour. The mixture was poured into saturated aqueous NaHCO3. The whole was extracted with ethyl acetate (30 mL×4), the combined organic layers washed with brine, dried over MgSO4, and concentrated in vacito. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (2:1) to provide the title compound (35 mg, 14% yield).

Workup

  1. stirringstirred for additional 1 hour
  2. extractionThe whole was extracted with ethyl acetate (30 mL×4)
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacito
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate-hexane (2:1)

Sources & evidence

ORD record
ord-37e833da938d425dbc34433ccd83c30a
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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