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

HRID 1510171Notes

Reaction equation

HRID 1510171 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 bicarbonate 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 chromatographed (ISCO, hexane/EtOAc, 0-40%, 40 min) to give 2.4 g of white solids. 1H NMR (DMSO-d6, 400 MHz): δ 6.95 (s, 1H), 4.19 (t, J=8.0 Hz, 2H), 3.04 (t, J=8.0 Hz, 2H), 2.26 (s, 3H), 2.23 (s, 3H), 2.18 (s, 3H).

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 chromatographed (ISCO, hexane/EtOAc, 0-40%, 40 min)

Sources & evidence

ORD record
ord-fa73682940774ec7ad1733ae2983170d
Source dataset
uspto-grants-2012_07
Patent number
US08211918B2

Reaction notes

Loading…