Toluene → dimethylindoline

HRID 1795414Notes

Reaction equation

HRID 1795414 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-4ab8d7938c534e5297f51406ce3776ad
Source dataset
uspto-grants-2006_04
Patent number
US07026476B2

Reaction notes

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