Hydrochloric Acid → 4,6-Dimethyl-5-nitroindoline

HRID 1510172Notes

Reaction equation

HRID 1510172 reaction equation
C([N:4]1[C:12]2[C:7](=[C:8]([CH3:17])[C:9]([N+:14]([O-:16])=[O:15])=[C:10]([CH3:13])[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.Cl>CO>[CH3:17][C:8]1[C:9]([N+:14]([O-:16])=[O:15])=[C:10]([CH3:13])[CH:11]=[C:12]2[C:7]=1[CH2:6][CH2:5][NH:4]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 107760451-Acetyl-4,6-dimethyl-5-nitroindoline

Product 1

HCID 105119384,6-Dimethyl-5-nitroindolineYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Acetyl-4,6-dimethyl-5-nitroindoline (2.4 g) was dissolved in methanol (25 ml). Hydrochloric acid 6N (20 ml) was added, followed by reflux for 15 hours. After the completion of the reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform, and the mixture was washed with saturated aqueous sodium bicarbonate and 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 1.8 g of 4,6-dimethyl-5-nitroindoline as yellow solids. 1H NMR (DMSO-d6, 400 MHz): δ 6.36 (brs, 1H, exchangeable with D2O, NH), 6.20 (s, 1H), 3.54 (t, J=8.0 Hz, 2H), 2.91 (t, J=8.0 Hz, 2H), 2.17 (s, 3H), 2.10 (s, 3H).

Workup

  1. temperatureby reflux for 15 hours
  2. customAfter the completion of the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe mixture was washed with saturated aqueous sodium bicarbonate and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was chromatographed (ISCO, hexane/EtOAc, 0-40%, 40 min)

Sources & evidence

ORD record
ord-c325b1f605c94cd79165eef492d028cd
Source dataset
uspto-grants-2012_07
Patent number
US08211918B2

Reaction notes

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