Dimethylformamide → 6-Methoxy-1,3,3-trimethylindolin-2-one

HRID 1243994Notes

Reaction equation

HRID 1243994 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][C:10](=O)N2)=C[CH:6]=1.[CH3:15]I.[CH3:17][N:18]([CH:20]=[O:21])[CH3:19]>>[CH3:3][O:4][C:5]1[CH:6]=[C:17]2[C:8]([C:9]([CH3:10])([CH3:15])[C:20](=[O:21])[N:18]2[CH3:19])=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27937496-Methoxyoxindole

Product 1

HCID 219318586-Methoxy-1,3,3-trimethylindolin-2-oneYield 83%

Procedure

To a stirred ice cold suspension of sodium hydride (60% in mineral oil, 3.9 g, 98.1 mmol) in 50 mL of dry DMF was added solid 6-methoxy-1,3-dihydro-indol-2-one (4.00 g, 24.5 mmol) portionwise over 10 minutes. To the resultant gray mixture was added dropwise MeI (2.68 g, 98.1 mmol). The mixture was warmed to room temperature and stirred for 45 minutes, and then was cooled back to 0° C. and quenched with 90 mL of water. The mixture was extracted with an ethyl acetate (EtOAc)/toluene mixture (2:1), and the extracts were dried with magnesium sulfate (MgSO4), treated with activated charcoal, filtered and concentrated to give a red syrup. Silica gel chromatography (1:10 EtOAc/hexanes) gave 4.16 g (83%) of the title compound as a white solid (mp 67–69° C.). Mass spectrum m/e calcd for M+H=234.1. Found 234.2.

Workup

  1. temperaturewas cooled back to 0° C.
  2. customquenched with 90 mL of water
  3. extractionThe mixture was extracted with an ethyl acetate (EtOAc)/toluene mixture (2:1)
  4. dry with materialthe extracts were dried with magnesium sulfate (MgSO4)
  5. additiontreated with activated charcoal
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a red syrup

Sources & evidence

ORD record
ord-8abe56ff1d8f40b59b6e5a7040960c98
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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