Dimethylformamide → Methyl (2,3-dihydro-1H-indol-1-yl)acetate

HRID 1601797Notes

Reaction equation

HRID 1601797 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[N:7]1([CH2:2][C:3]([O:5][CH3:6])=[O:4])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10328IndolineHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 22199910Methyl (2,3-dihydro-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.40 ml of methyl bromoacetate was added dropwise to a mixture of 0.25 g of indoline, 2 ml of dimethylformamide and 0.87 g of anhydrous potassium carbonate, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.30 g of the title compound having Rf=0.63 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. extractionafter which it was extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-c363ad43604b4294b34e7923a0fe2cd0
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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