Nitric Acid → HCID 15538699, compound

HRID 1597189Notes

Reaction equation

HRID 1597189 reaction equation
[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:26]([O-])([OH:28])=[O:27]>C(O)(=O)C>[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[N:15]([CH3:24])[C:14]2=[O:25])=[C:11]([N+:26]([O-:28])=[O:27])[C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15544298HCID 15544298, compound

Product 1

HCID 15538699HCID 15538699, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-[7-Fluoro-2H-1,4-benzoxazine-3(4H)-on-6-yl]-1-methyl-6-trifluoromethyl-2,4-(1H, 3H)-pyrimidinedione (3.5 g) was slowly added to a mixture of acetic acid (15 ml) and fuming nitric acid (45 ml) at 0° C. with stirring. After stirring for 2 hr at room temperature, the solution was poured on ice-water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel using hexane-ethyl acetate (6:4) as eluent to afford the title compound (3.25 g).

Workup

  1. stirringAfter stirring for 2 hr at room temperature
  2. additionthe solution was poured on ice-water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5ca21aa1950f41d191450a69dc8c3252
Source dataset
uspto-grants-2001_09
Patent number
US06294503B1

Reaction notes

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