Water → 2,6,6-Trimethyl-6,7-dihydro-1H-indol-4(5H)-one

HRID 900481Notes

Reaction equation

HRID 900481 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:7][C:6](=[O:8])[CH:5]([CH2:9][C:10](=O)[CH3:11])[C:4](=O)[CH2:3]1.C([O-])(=O)C.[NH4+:19].O>C(O)(=O)C>[CH3:11][C:10]1[NH:19][C:4]2[CH2:3][C:2]([CH3:14])([CH3:1])[CH2:7][C:6](=[O:8])[C:5]=2[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 14733595,5-dimethyl-2-(2-oxopropyl)cyclohexane-1,3-dione

Product 1

HCID 12348692,6,6-Trimethyl-6,7-dihydro-1H-indol-4(5H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

The crude tri-ketone from Example 37 was dissolved in 300 mL of acetic acid to which ammonium acetate (55 g, 0.714 mmol) was added. The reaction mixture was heated at 65° C. until all starting material had disappeared (2-3 h), cooled to RT, added to H2O, and washed with EtOAc. The organic layer was washed with saturated NaHCO3 (×3), brine (×1) and dried over MgSO4. Solvent was removed in vacuo and the oily residue was passed through a plug of silica. The appropriate fractions were collected and solvent was removed. The resulting solid was washed with EtOAc and hexanes (if too much hexanes is added the material crashing back out of solution after the addition of EtOAc will be gummy. To remedy this simply add a little EtOAc). The solid was filtered and washed with hexanes. More solid can be recovered by removing the solvent and repeating this procedure. LCMS m/z M+H=178.1. Approximately 5 g of a tan solid was collected and identified as 2,6,6-trimethyltetrahydroindol-4-one.

Workup

  1. additionwas added
  2. custom(2-3 h)
  3. temperaturecooled to RT
  4. washwashed with EtOAc
  5. washThe organic layer was washed with saturated NaHCO3 (×3), brine (×1)
  6. dry with materialdried over MgSO4
  7. customSolvent was removed in vacuo
  8. customThe appropriate fractions were collected
  9. customsolvent was removed
  10. washThe resulting solid was washed with EtOAc and hexanes (if too much hexanes
  11. additionis added the material
  12. additionafter the addition of EtOAc
  13. additionthis simply add a little EtOAc)
  14. filtrationThe solid was filtered
  15. washwashed with hexanes
  16. customMore solid can be recovered
  17. customby removing the solvent
  18. customApproximately 5 g of a tan solid was collected

Sources & evidence

ORD record
ord-6e1666e88df245c291e886ee855b7608
Source dataset
uspto-grants-2008_04
Patent number
US07358370B2

Reaction notes

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