Potassium Carbonate → 1-Methacryloylindoline-2-carboxylic acid ethyl ester

HRID 745608Notes

Reaction equation

HRID 745608 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(=O)([O-])[O-].[K+].[K+].[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>C(Cl)Cl>[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:21](=[O:25])[C:22]([CH3:24])=[CH2:23])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13528Methacryloyl chlorideHCID 11949691Ethyl Indoline-2-carboxylate

Product 1

HCID 127642221-Methacryloylindoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The starting material is prepared as follows: To the mixture of 3.0 g of indoline-2-carboxylic acid ethyl ester, 4.3 g of powdered potassium carbonate and 30 ml of methylene chloride is added 1.64 g of methacryloyl chloride in 5 ml of methylene chloride during 1 minute. After stirring at room temperature for 3 hours the mixture is partitioned between 50 ml of water and 100 ml of diethyl ether. The organic layer is washed with 30 ml of 1N hydrochloric acid and 25 ml of saturated sodium chloride, dried and evaporated, to yield the 1-methacryloylindoline-2-carboxylic acid ethyl ester as an oil.

Workup

  1. customThe starting material is prepared
  2. customis partitioned between 50 ml of water and 100 ml of diethyl ether
  3. washThe organic layer is washed with 30 ml of 1N hydrochloric acid and 25 ml of saturated sodium chloride
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-d26919af8b764bb38c5de7eb5423c9c8
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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