Methyl iodide → 3-Methyloxindole

HRID 2307833Notes

Reaction equation

HRID 2307833 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li][CH2:12]CCC.CI>C1COCC1>[CH3:12][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 321710OxindoleHCID 178418339Butyllithium

Product 1

HCID 1509233-MethyloxindoleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of oxindole (665 mg, 5.0 mmol) in THF (10 ml) was treated dropwise with n-BuLi (4.4 ml, 11.0 mmol) at −78° C., stirred for 30 min. at −78° C. To the reaction methyliodine (2 ml) was added dropwise at −78° C. The resulting solution was warmed up to room temperature. The mixture was quenched with water. The reaction solution was partitioned between ethylacetate and water. The organic layer was washed (brine), dried (Na2SO4), filtered and concentrated under vacumm. Purification on silica gel with 30% ethyl acetate/hexane to provide the title compound (630 mg, 86%). MS (DCI/NH3) m/e 148 (M+1)+.

Workup

  1. additionwas added dropwise at −78° C
  2. temperatureThe resulting solution was warmed up to room temperature
  3. customThe mixture was quenched with water
  4. customThe reaction solution was partitioned between ethylacetate and water
  5. washThe organic layer was washed (brine)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacumm
  9. customPurification on silica gel with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-363776a8a5a54557967dc469c0c041cc
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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