Dimethylformamide → 1,3,3,7-Tetramethylindolin-2-one

HRID 469367Notes

Reaction equation

HRID 469367 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1N[C:10](=O)[CH2:9]2.IC.[CH3:16][N:17]([CH:19]=[O:20])[CH3:18]>>[CH3:16][N:17]1[C:18]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:10])[C:4]([CH3:12])([CH3:3])[C:19]1=[O:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 30142252H-Indol-2-one, 1,3-dihydro-7-methyl-

Product 1

HCID 130305951,3,3,7-Tetramethylindolin-2-one

Procedure

2.00 g (50.0 mmol) sodium hydride (55%, suspension in mineral oil) were added at 0° C. to 2.34 g (3.58 mmol) 7-methyl-1,3-dihydro-indol-2-one in 20 mL DMF and the mixture was stirred for 30 min. Then 3.00 mL (48.2 mmol) iodomethane were added and the mixture was stirred for 2 h at RT. Ice water was added to the reaction mixture, then it was extracted with DCM and aqueous sodium hydrogen carbonate solution. The organic phase was dried on sodium sulphate, filtered and evaporated down i. vac. The residue was purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. stirringthe mixture was stirred for 2 h at RT
  2. extractionit was extracted with DCM and aqueous sodium hydrogen carbonate solution
  3. customThe organic phase was dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe residue was purified by preparative HPLC-MS
  7. additionThe fractions containing the product
  8. customfreeze-dried

Sources & evidence

ORD record
ord-42325dfd7d47419f9a71ff0b27de742f
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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