Ethyl Acetate → HCID 2887745, compound

HRID 1645399Notes

Reaction equation

HRID 1645399 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[C:13]([O-])([O-])=O.[K+].[K+].C([O:22][CH2:23][CH3:24])(=O)C>CC(C)=O>[OH:12][C:5]1([CH2:13][C:23](=[O:22])[CH3:24])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[NH:7][C:6]1=[O:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 118405-Methylisatin

Product 1

HCID 2887745HCID 2887745, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Methylisatin 45 (10 mmol, Lancaster, order no. 8009) was dissolved in acetone 46 (50 ml), K2CO3 (138 mg, 1 mmol) was added, and the mixture was stirred at room temperature for 24 hours. The course of the reaction was monitored by TLC (eluent: ethyl acetate). The reaction solution was worked up by concentrating to 40 ml in vacuo, during which the product started to precipitate. To complete the precipitation the solution was cooled to approx. 10° C. in a refrigerator overnight. The product which precipitated was filtered out with suction and dried in vacuo. It was possible to isolate further reaction product by removing the acetone completely and dissolving the residue which remained in ethyl acetate. The solid formed during subsequent precipitation with hexane was filtered out with suction and dried in vacuo.

Workup

  1. concentrationby concentrating to 40 ml in vacuo, during which the product
  2. customto precipitate
  3. customthe precipitation the solution
  4. temperaturewas cooled to approx. 10° C. in a refrigerator overnight
  5. customThe product which precipitated
  6. filtrationwas filtered out with suction
  7. customdried in vacuo
  8. customto isolate further reaction product
  9. customby removing the acetone completely
  10. dissolutiondissolving the residue which
  11. customThe solid formed during subsequent precipitation with hexane
  12. filtrationwas filtered out with suction
  13. customdried in vacuo

Sources & evidence

ORD record
ord-fcda2bda06ee4c2abc0eaa536a00f886
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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