Nitric Acid → HCID 12130786, compound

HRID 581917Notes

Reaction equation

HRID 581917 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[N+:18]([O-])([OH:20])=[O:19]>>[N+:18]([C:5]1[CH:6]=[C:1]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=1)([O-:20])=[O:19]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 18923Pyrimidine, 4-phenyl-

Product 1

HCID 12130786HCID 12130786, compoundYield 50%

Conditions

Temperature
0 °C

Procedure

A mixture of 4-phenylpyrimidine (10 g, 64 mmol) and conc. H2SO4 (33 ml) was added to a mixture of conc. H2SO4 (22 ml) and conc. HNO3 (16 ml) at 0° C. The resulting mixture was stirred at 0° C. for 2 hr, poured onto crushed ice, and extracted with CH2Cl2. The extract was washed with a 5% aqueous NaHCO3 solution, dried over MgSO4 and concentrated under reduced pressure. The residue was triturated with isopropanol and the precipitate was filtered off and dried under reduced pressure to give (57) (6.4 g, 50%).

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionextracted with CH2Cl2
  4. washThe extract was washed with a 5% aqueous NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with isopropanol
  8. filtrationthe precipitate was filtered off
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-b8b721cdadab41be81c95df26252b943
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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