Dimethyl Sulfate → 1,3-Dihydro-5-methoxy-1-methyl-2H-indol-2-one

HRID 447402Notes

Reaction equation

HRID 447402 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2.[CH3:15]OS(OC)(=O)=O>C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:15])[C:9](=[O:14])[CH2:8]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 15142865-Methoxyoxindole

Product 1

HCID 91021941,3-Dihydro-5-methoxy-1-methyl-2H-indol-2-oneYield 53.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A dry round-bottom flask was charged with NaH (60% wt) (64 mg, 1.61 mmol) and toluene (2.0 mL). The suspension was heated to 100° C. and then 5-methoxyindolin-2-one (250 mg, 1.53 mmol) was added. After 30 min at 100° C., Me2SO4 (0.16 mL, 1.68 mmol) was added and the temperature maintained at 100° C. for 2.5 h. The reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, hexanes/EtOAc, 3:1 to 2:1) to give the product as a beige solid (144 mg, 53%); MS ESI 164.1 [M+H]+, calcd for [C9H9NO2+H]+ 164.07.

Workup

  1. temperaturethe temperature maintained at 100° C. for 2.5 h
  2. temperatureThe reaction was cooled to room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by column chromatography (silica gel, hexanes/EtOAc, 3:1 to 2:1)

Sources & evidence

ORD record
ord-a61b0949a52f417a8a579a9ef33bf2fe
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

Loading…