Nitric Acid → HCID 22402915, compound

HRID 375070Notes

Reaction equation

HRID 375070 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:7][O:8][C:4]=2[CH:3]=1.[N+:16]([O-])([OH:18])=[O:17]>>[F:1][C:2]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:5]2[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 22402921HCID 22402921, compound

Product 1

HCID 22402915HCID 22402915, compound

Conditions

Temperature
0 °C

Procedure

Methyl 6-fluoro-1,2-benzisoxazole-3-acetate (6.0 g, 28.7 mmol) is added portionwise to nitric acid (90%, 60 mL) at 0° C. The reaction mixture is stirred at 0° C. for 30 minutes and poured into an ice/water mixture. The aqueous mixture is extracted with methylene chloride. The organic extracts are combined, washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow oil. Flash column chromatography of the oil using silica gel and ether/petroleum ether solutions gives the title product as a pale yellow solid which is identified by 1HNMR spectral analysis.

Workup

  1. extractionThe aqueous mixture is extracted with methylene chloride
  2. washwashed sequentially with water, saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow oil

Sources & evidence

ORD record
ord-8642462bfa7d466e95772403a8c654e3
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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