Nitric Acid → HCID 21698924, compound

HRID 1597188Notes

Reaction equation

HRID 1597188 reaction equation
[F:1][C:2]1[C:12]([N:13]2[CH:18]([CH3:19])[N:17]([CH:20]([F:22])[F:21])[C:16](=[O:23])[CH2:15][NH:14]2)=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:24]([O-])([OH:26])=[O:25]>C(O)(=O)C>[F:1][C:2]1[C:12]([N:13]2[CH:18]([CH3:19])[N:17]([CH:20]([F:21])[F:22])[C:16](=[O:23])[CH2:15][NH:14]2)=[C:11]([N+:24]([O-:26])=[O:25])[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 21698926HCID 21698926, compound

Product 1

HCID 21698924HCID 21698924, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[7-Fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4-difluoromethyl-3-methyl-1,4-dihydro-1,2,4-triazin-5-one (0.38 g) was dissolved in acetic acid (10 ml) and fuming nitric acid (10 ml) was added slowly at ambient temperature. The resulting mixture was stirred for 1 hour and poured into ice-water. The mixture was extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel eluted with ethyl acetate and hexanes (1:3) to give title compound (0.17 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluted with ethyl acetate and hexanes (1:3)

Sources & evidence

ORD record
ord-85a2e174581c4937991e1b203f1d1ded
Source dataset
uspto-grants-2001_09
Patent number
US06294503B1

Reaction notes

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