Nitric Acid → 1-Acetyl-4,6-dimethyl-5-nitroindoline

HRID 2296891Notes

Reaction equation

HRID 2296891 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N+:15]([O-])([OH:17])=[O:16].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[C:9]([N+:15]([O-:17])=[O:16])=[C:10]([CH3:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 98556931-Acetyl-4,6-dimethylindoline

Product 1

HCID 107760451-Acetyl-4,6-dimethyl-5-nitroindoline

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

1-Acetyl-4,6-dimethylindoline (2.6 g) was dissolved in acetic anhydride (35 ml), and nitric acid (d=1.5, 0.92 ml) dissolved in acetic anhydride (15 ml) was added dropwise at 0° C. The mixture was stirred at room temperature for one hour and poured into ice water. Saturated aqueous sodium hydrogencarbonate was added to neutralize the mixture, and the mixture was extracted with chloroform. The extract was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent:chloroform-methanol=1:0-100:1) to give 2.4 g of the title compound (2).

Workup

  1. additionwas added dropwise at 0° C
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent:chloroform-methanol=1:0-100:1)

Sources & evidence

ORD record
ord-9e861eeec9fe4bfeb17ddd4eb298ae8e
Source dataset
uspto-grants-2002_12
Patent number
US06489475B2

Reaction notes

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