Nitric Acid → HCID 57566537, compound

HRID 1663196Notes

Reaction equation

HRID 1663196 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-2fac080a6a924f74bf725e105ba1f88e
Source dataset
uspto-grants-2011_10
Patent number
US08034832B2

Reaction notes

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