Toluene → dimethylindoline

HRID 431534Notes

Reaction equation

HRID 431534 reaction equation
C[C:2]1(C)C2[C:5](=CC=CC=2)[NH:4][C:3]1=O.COCCO[AlH2-]OCCOC.[Na+].[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:2][CH:3]1[CH2:31][C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]1[CH3:5]

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 16684438Red-Al

Product 1

HCID 583485dimethylindolineYield 60%

Conditions

Temperature
100 °C

Procedure

A solution of dimethyl oxindole (220 mg, 1.4 mmol) in toluene (5 mL) was treated with 65% Red-Al solution in toluene (0.64 mL, 2.05 mmol) at 80° C. After stirring at 100° C. for 4 h, the reaction mixture was quenched with 1N sodium hydroxide solution. The organic layer was separated, washed with water and brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluent: 25% EtOAc in hexanes) to give dimethyl indoline as a light blue oil (121 mg, 60%).

Workup

  1. customthe reaction mixture was quenched with 1N sodium hydroxide solution
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluent: 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c2d35a28d71d4c3eb6fe23c9b7652ec7
Source dataset
uspto-grants-2003_12
Patent number
US06660732B2

Reaction notes

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