Dimethylformamide → Ethyl 2,3-dihydro-1H-indole-1-acetate

HRID 1374839Notes

Reaction equation

HRID 1374839 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[N:1]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 10328IndolineHCID 11430Potassium Carbonate

Product 1

HCID 22199911Ethyl 2,3-dihydro-1H-indole-1-acetateYield 73.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Indoline (1.07 g, 8.98 mmol), ethyl bromoacetate (1.20 ml, 10.8 mmol), potassium carbonate (2.10 g, 15.2 mmol) were added to dimethylformamide (14 ml), and the mixture was heated at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature and diluted with ethyl acetate, and then washed with water and dried over sodium sulfate. Insoluble solids were removed by filtration and the filtrate was evaporated under reduced pressure. The resulting oil was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound as yellow oil (1.35 g, yield: 73%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customInsoluble solids were removed by filtration
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe resulting oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-f8ffaeffe3d04dc9899b108182b84d00
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

Loading…