Triethylamine → HCID 12842039, compound

HRID 1659299Notes

Reaction equation

HRID 1659299 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 12842039HCID 12842039, compoundYield 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-1c657ac54a894a438cc6d1d1662d57d4
Source dataset
uspto-grants-1981_12
Patent number
US04303583

Reaction notes

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