Nitric Acid → HCID 86721378, compound

HRID 869545Notes

Reaction equation

HRID 869545 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16].[OH-].[Na+]>C(OC(=O)C)(=O)C>[F:1][C:2]1[N:7]=[C:6]([N+:15]([O-:17])=[O:16])[C:5]([NH:8][C:9]([CH:11]2[CH2:12][CH2:13][CH2:14]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 86721377HCID 86721377, compound

Product 1

HCID 86721378HCID 86721378, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

[step 2] N-(6-fluoropyridin-3-yl)cyclobutanecarboxamide (800 mg, 4.12 mmol) obtained in step 1 was dissolved in acetic anhydride (4 mL), fuming nitric acid (0.7 mL, 15.7 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Under ice-cooling, 5 mol/L aqueous sodium hydroxide solution was added dropwise to the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 v/v) to give N-(6-fluoro-2-nitropyridin-3-yl)cyclobutanecarboxamide (348 mg, 35%).

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 v/v)

Sources & evidence

ORD record
ord-e946f7af2a9842c5ba9dbfd7981eefa6
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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