Hydrochloric Acid → 1-ethyl-5-methyl-1,3-dihydro-2H-indol-2-one

HRID 1158732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158732
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5](=O)[C:4]1=[O:14])[CH3:2].O.NN.Cl>CCOC(C)=O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:14])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 24713051-ethyl-5-methyl-2,3-dihydro-1H-indole-2,3-dione

Produkt 1

HCID 112753291-ethyl-5-methyl-1,3-dihydro-2H-indol-2-oneAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 1-ethyl-5-methyl-1H-indole-2,3-dione (ix-a, 1.53 g, 8.09 mmol) and hydrazine monohydrate (30 mL, 618 mmol) was heated to 110° C. After 5 h, the reaction was cooled to RT and conc. HCl was added to adjust the reaction mixture to approximately pH 3. The mixture was stirred overnight, and poured into a separatory funnel containing EtOAc (150 mL). The mixture was shaken and the layers were separated. The aqueous layer was extracted with EtOAc (2×150 mL) and the combined organic layers were dried, filtered and concentrated to give 1-ethyl-5-methyl-1,3-dihydro-2H-indol-2-one (i-a, 1.03 g, 72.5%). NH4OAc QC conditions. DAD Retention time =1.48 min. M+H=176.

Aufarbeitung

  1. temperaturethe reaction was cooled to RT
  2. additionpoured into a separatory funnel
  3. stirringThe mixture was shaken
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
  6. customthe combined organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4ad9e0603b8748fc82f82b40d4c483bf
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812018B2

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