Nitric Acid → HCID 57566537, compound

HRID 563967Notes

Reaction equation

HRID 563967 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-9ea1658fe69746ae94635b16e6074778
Source dataset
uspto-grants-2011_11
Patent number
US08067606B2

Reaction notes

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