Triethylamine → 1-Methacryloylindoline-2-carboxylic acid ethyl ester

HRID 1262913Notes

Reaction equation

HRID 1262913 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:26])[C:23]([CH3:25])=[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:26])[C:23]([CH3:25])=[CH2:24])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 11949691Ethyl Indoline-2-carboxylate

Product 1

HCID 127642221-Methacryloylindoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a chilled and stirred mixture of 2,3-dihydroindole-2-carboxylic acid ethyl ester (4.78 g., 25.0 mmole), triethylamine (2.7 g., 26.7 mmole), and anhydrous ether (500 ml) was added dropwise methacryloyl chloride (2.9 g., 27.7 mmole) dissolved in a small amount of ether. After the completion of the addition, the ice bath was removed, and the reaction mixture was stirred for 4 hours. The precipitate which separated was removed by filtration, and the filter residue was washed with ether. The combined filtrate and washing were washed with water (two 700ml portions), then with saline, and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure on a rotary evaporator gave the product as an oil. The product was purified by preparative HPLC (Prep LC/System 500, Waters Associates), using a micro porasil column eluted with a mixture of hexane (95%) and ethyl acetate (5%). The crude oil may be used directly in the following reaction (Example 2).

Workup

  1. temperatureTo a chilled
  2. additionAfter the completion of the addition
  3. customthe ice bath was removed
  4. stirringthe reaction mixture was stirred for 4 hours
  5. customThe precipitate which separated
  6. customwas removed by filtration
  7. washthe filter residue was washed with ether
  8. washThe combined filtrate and washing
  9. washwere washed with water (two 700ml portions)
  10. dry with materialwith saline, and dried over anhydrous magnesium sulfate
  11. customEvaporation of the solvent under reduced pressure
  12. customon a rotary evaporator

Sources & evidence

ORD record
ord-e4704e1328bc4b7aac92205cf057673c
Source dataset
uspto-grants-1984_06
Patent number
US04454291

Reaction notes

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