Nitric Acid → HCID 67233431, compound

HRID 1671651Notes

Reaction equation

HRID 1671651 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:20])[CH:9]=[CH:10][C:11]=1[CH:12]1[CH2:16][CH2:15][C:14](=[O:17])[O:13]1.C(=O)(O)[O-].[Na+]>>[F:5][C:6]1[C:11]([CH:12]2[CH2:16][CH2:15][C:14](=[O:17])[O:13]2)=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[C:8]([NH:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:20])[CH:7]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 67350605HCID 67350605, compound

Product 1

HCID 67233431HCID 67233431, compound

Procedure

Fuming nitric acid (3 ml) was added to N-(3-fluoro-4-(5-oxotetrahydrofuran-2-yl)phenyl)pyridine-2-carboxamide (600 mg) obtained in (step 4), and the reaction liquid was stirred at room temperature for 2 hours. With cooling with ice, aqueous saturated sodium bicarbonate was added to the reaction liquid to make it basic, and extracted with ethyl acetate. This was dried with anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was washed with chloroform/hexane mixed solvent to obtain the entitled compound.

Workup

  1. customobtained in (step 4)
  2. customthe reaction liquid
  3. additionwas added to the reaction liquid
  4. extractionextracted with ethyl acetate
  5. dry with materialThis was dried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. washthe resulting residue was washed with chloroform/hexane mixed solvent
  8. customto obtain the entitled compound

Sources & evidence

ORD record
ord-a4af615194fb4c57878330f7c5c1cc28
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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