Oxalyl chloride → 4,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

HRID 1826252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1826252
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[NH2:7].[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15]>CO>[CH3:12][O:11][C:9]1[CH:10]=[C:4]([O:3][CH3:2])[CH:5]=[C:6]2[C:8]=1[C:13](=[O:17])[C:14](=[O:15])[NH:7]2

Komponenten

4

Edukt 2

HCID 65578Oxalyl chlorideHCID 218603Benzenamine, 3,5-dimethoxy-, hydrochloride (1:1)

Produkt 1

HCID 115575224,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3,5-dimethoxyaniline hydrochloride (54.7 g), oxalyl chloride (54 ml) and methanol (500 ml) was stirred and heated to reflux for 1.5 hours. The mixture was cooled to ambient temperature. The precipitate was isolated, washed in turn with methanol and diethyl ether and dried under vacuum to give 4,6-dimethoxy-2,3-dioxoindoline (55 g); NMR Spectrum: (DMSOd6) 3.85 (s, 3H), 3.9 (s, 3H), 6.0 (s, 1H), 6.2 (s, 1H), 10.9 (s, 1H); Mass Spectrum: M+Na+ 230.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. customThe precipitate was isolated
  4. washwashed in turn with methanol and diethyl ether
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7fd88c2de5234efa83bc73fc3aed1068
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049438B2

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