Ethyl 3-methylsulphanyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylate → Ethyl 2-oxoindoline-5-carboxylate

HRID 241722

Reaktionsgleichung

Reaktionsgleichung von HRID 241722
CS[CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[NH:5][C:4]1=[O:17]>C(O)(=O)C.[Zn]>[O:17]=[C:4]1[CH2:3][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[NH:5]1

Komponenten

4

Edukt 1

HCID 12351489Ethyl 3-methylsulphanyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylate

Produkt 1

HCID 13077452Ethyl 2-oxoindoline-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of the compound obtained in Step A (0.1448 mol) in glacial acetic acid (700 ml) there is added powdered zinc (0.8690 mol). The two-phase mixture is stirred at 40° C. for 8 hours. The reaction mixture is filtered and the filtrate is then evaporated to dryness. The residue is stirred in water overnight and filtered and the precipitate obtained is washed with water. The product is taken up in toluene and then evaporated to dryness, and is then taken up in ether, filtered, washed with ether and then dried in vacuo at 40° C. under P2O5 to yield the title product, which is used directly in the next Step.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is then evaporated to dryness
  3. stirringThe residue is stirred in water overnight
  4. filtrationfiltered
  5. customthe precipitate obtained
  6. washis washed with water
  7. customevaporated to dryness
  8. filtrationfiltered
  9. washwashed with ether
  10. customdried in vacuo at 40° C. under P2O5

Quellen und Nachweise

ORD-Eintrag
ord-dd0897eee5ad448ca81cab28f8aaab8a
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653073B2

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