Sodium Sulfate → 3,3-Dimethylindoline

HRID 74517Notes

Reaction equation

HRID 74517 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][C:8]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 118049123,3-Dimethylindoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere a solution of 6.20 mL (6.20 mmol) of a 1M solution lithium aluminium hydride in THF and 10 mL THF was slowly added dropwise to 1.00 g (6.20 mmol) 3,3-dimethyl-1,3-dihydro-indol-2-one in 50 mL THF. Then the reaction mixture was heated to 60° C. for 1 h. After cooling to 0° C., 3 mL ice water were slowly added dropwise. 20 g sodium sulphate were added and the mixture was suction filtered. The solution was evaporated down i. vac.

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationfiltered
  3. customThe solution was evaporated down i

Sources & evidence

ORD record
ord-42118fc52b51418486d46e726a4a3fb4
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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