Nitric Acid → HCID 86686556, compound

HRID 1528067Notes

Reaction equation

HRID 1528067 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:13])([CH3:12])[C:5](=[O:11])[NH:6]2.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[F:1][C:2]1[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:13])([CH3:12])[C:5](=[O:11])[NH:6]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 248243364-Fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 86686556HCID 86686556, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 4-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.1 g) in concentrated sulfuric acid (60 mL) was added dropwise a mixture of fuming nitric acid (0.99 mL) and concentrated sulfuric acid (10 mL) over 30 min at −30° C. The reaction mixture was stirred between −30° C. to 0° C. for 30 min, and poured into ice. The resulting solid was collected by filtration, washed with water, and dissolved in ethyl acetate. The obtained solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.2 g).

Workup

  1. additionpoured into ice
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate
  5. washThe obtained solution was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-edeea989b2344b3ca00cc625e82c097a
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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