Ethyl Acetate → HCID 2728520, compound

HRID 1645401Notes

Reaction equation

HRID 1645401 reaction equation
[F: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>[F: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([OH:12])[CH2:13][C:23](=[O:22])[CH3:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2365665-Fluoroisatin

Product 1

HCID 2728520HCID 2728520, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

5-Fluoroisatin 32 (10 mmol, Lancaster, order no. 14553) was dissolved in acetone 46 (50 ml), K2CO3 (138 mg, 1 mmol) was added, and the mixture was stirred at room temperature for 5 hours. The course of the reaction was monitored by TLC (eluent: ethyl acetate). To work up the product the acetone was completely distilled off in vacuo. The residue was dissolved in ethyl acetate, and the solution was filtered over silica gel with ethyl acetate. The filtrate was concentrated to 20 ml, and hexane was added until precipitation started. 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. The resulting crude product was recrystallized from ethyl acetate/hexane (1:4).

Workup

  1. distillationwas completely distilled off in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. filtrationthe solution was filtered over silica gel with ethyl acetate
  4. concentrationThe filtrate was concentrated to 20 ml, and hexane
  5. additionwas added until precipitation
  6. customthe precipitation
  7. temperaturethe solution was cooled to approx. 10° C. in a refrigerator overnight
  8. customThe product which precipitated
  9. filtrationwas filtered out with suction
  10. customdried in vacuo
  11. customThe resulting crude product was recrystallized from ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-0cc5eb7eb79140d4868715d20ae26da1
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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