Nitric Acid → HCID 57566537, compound

HRID 1929601Notes

Reaction equation

HRID 1929601 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[N+:15]([O-])([OH:17])=[O:16]>OS(O)(=O)=O.O>[F:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[C:4]([C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 45117400HCID 45117400, compound

Product 1

HCID 57566537HCID 57566537, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a room temperature solution of 2-(3,5-difluoro-phenyl)-pyrimidine (1.2 g, 6.24 mmole) in H2SO4 (3 mL) was added 90% HNO3 (0.375 mL, 9.37 mmoles) over 10 seconds via syringe. The resulting mixture was stirred at room temperature for 1 hour then poured into ice. The resulting heterogeneous mixture was then diluted with water, warmed to room temperature, and filtered. The solids were washed with water and dried in vacuo to afford the title compound (1.53 g, 100%) as a tan solid. 1H NMR (dmso-d6, 500 MHz): 8.92 (d, 2H); 8.67 (m, 1H); 7.94 (m, 1H); 7.65 (dd, 1H).

Workup

  1. additionthen poured into ice
  2. temperaturewarmed to room temperature
  3. filtrationfiltered
  4. washThe solids were washed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9f2eb3d4087a43039bd4819ce7f8b2d5
Source dataset
uspto-grants-2012_05
Patent number
US08188095B2

Reaction notes

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