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4-Nitro-1H-indole → Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

HRID 74571
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74571
P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)([O-:12])=[O:11].[O:22]=[C:23](N1CCCC1)[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])O.[Na+]>CO>[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:23](=[O:22])[C:24]([O:26][CH3:27])=[O:25])=[CH:16][NH:17]2)([O-:12])=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1457664-Nitro-1H-indoleHCID 516892Sodium BicarbonateHCID 4432411Diphosphoryl tetrachlorideHCID 10975749Methyl oxo-pyrrolidin-1-yl-acetate

Produkt 1

HCID 10243717Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

9.4 mL (68 mmol) diphosphoryl chloride were slowly added dropwise to 10 g (62 mmol) 4-nitroindole and 11 g (68 mmol) methyl oxo-pyrrolidin-1-yl-acetate with stirring and while cooling with ice. The reaction mixture was heated to RT and stirred for 3 h at RT. Then first of all 10 mL MeOH were added dropwise at 0° C. and then saturated sodium hydrogen carbonate solution was added dropwise at 0° C. After repeated extraction with DCM the organic phase was dried and evaporated down to 100 mL. This residue was left to stand at RT and the precipitate formed was suction filtered, washed and dried in the air.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. stirringstirred for 3 h at RT
  3. extractionextraction with DCM the organic phase
  4. customwas dried
  5. customevaporated down to 100 mL
  6. waitThis residue was left
  7. customto stand at RT
  8. customthe precipitate formed
  9. filtrationfiltered
  10. washwashed
  11. customdried in the air

Quellen und Nachweise

ORD-Eintrag
ord-68e5f506e7274640bd5fd8e1e106861a
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829006B2

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