Toluene → dimethylindoline

HRID 431041Notes

Reaction equation

HRID 431041 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 IN 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 IN 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-61cdef5924334d99b196ba02d349f9e1
Source dataset
uspto-grants-2003_12
Patent number
US06656933B2

Reaction notes

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