Sodium Bicarbonate → 1-Acetyl-4,6-dimethylindoline

HRID 507328Notes

Reaction equation

HRID 507328 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:12]([BH3-])#N.[Na+].[C:16](=[O:19])(O)[O-].[Na+]>C(O)(=O)C>[C:16]([N:6]1[C:7]2[C:3](=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:11])[CH:8]=2)[CH2:4][CH2:5]1)(=[O:19])[CH3:12]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 98339914,6-dimethyl-1H-indole

Product 1

HCID 98556931-Acetyl-4,6-dimethylindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4,6-Dimethylindole (1.08 g) was dissolved in acetic acid (20 ml), and sodium cyanoborohydride (2.3 g) was added portionwise at 15° C. The mixture was stirred at said 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 ethyl acetate. The extract was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in benzene, and acetic anhydride (840 mg) was added, which was followed by stirring at room temperature for one hour. The reaction 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 1.3 g of 1-acetyl-4,6-dimethylindoline.

Workup

  1. customfor one hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in benzene
  7. additionacetic anhydride (840 mg) was added
  8. stirringby stirring at room temperature for one hour
  9. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate and saturated brine
  10. dry with materialdried over sodium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customThe residue was chromatographed (ISCO, hexane/EtOAc, 0-40%, 40 min)

Sources & evidence

ORD record
ord-78222f0fd9624fde88fc2b1240752a9e
Source dataset
uspto-grants-2010_08
Patent number
US07786146B2

Reaction notes

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