Nitric Acid → HCID 19365524, compound

HRID 849929Notes

Reaction equation

HRID 849929 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:18]=2)=[CH:9][CH:8]=1.[N+:25]([O-])([OH:27])=[O:26]>>[F:6][C:7]1[C:8]([N+:25]([O-:27])=[O:26])=[CH:9][C:10]([C:13]2[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:21])([F:20])[F:22])=[CH:17][N:18]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 19365516HCID 19365516, compound2×

Product 1

HCID 19365524HCID 19365524, compoundYield 85%

Procedure

To 2.5 ml of concentrated sulfuric acid was added 0.34 g of 3-(4-fluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-4) at 5° C. Furthermore, 0.13 ml of 61% nitric acid was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was added to ice water, followed by extraction with ethyl acetate. The organic layer was washed with water and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 0.337 g (yield, 85%) of 3-(4-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-13; m.p., 134.4° C.).

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-536a9a27a43e4599a60f44cf775ae753
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

Loading…