Triethylamine → 2,3-Dihydro-1-(1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 851545Notes

Reaction equation

HRID 851545 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>CCOCC>[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]1[C:22](=[O:25])[CH:23]=[CH2:24])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 11949691Ethyl Indoline-2-carboxylate

Product 1

HCID 128420392,3-Dihydro-1-(1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl esterYield 78.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a chilled and stirred mixture of 2,3-dihydroindole-2-carboxylic acid ethyl ester (14.34 g.), triethylamine (7.65 g.) and anhydrous ether (600 ml.) was added dropwise acryloyl chloride (7.1 g.) dissolved in a small amount of ether. The ice bath was removed, and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was chilled in ice, then a precipitate was removed by filtration. The filter residue was washed with ether. The combined filtrate and washing were washed with water, then with saline, and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure on a rotary evaporator gave the titled compound (14.4 g.) as an oil.

Workup

  1. temperatureTo a chilled
  2. customThe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 4 hours
  4. temperatureThe reaction mixture was chilled in ice
  5. customa precipitate was removed by filtration
  6. washThe filter residue was washed with ether
  7. washThe combined filtrate and washing
  8. washwere washed with water
  9. dry with materialwith saline, and dried over anhydrous magnesium sulfate
  10. customEvaporation of the solvent under reduced pressure
  11. customon a rotary evaporator

Sources & evidence

ORD record
ord-2652f5e2ea2f450ca636c0759cf4ec5c
Source dataset
uspto-grants-1983_05
Patent number
US04385180

Reaction notes

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