methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate → methyl 3-(4-aminophenyl)-1H-pyrrole-2-carboxylate

HRID 227666

Reaktionsgleichung

Reaktionsgleichung von HRID 227666
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[CH:13][NH:12][C:11]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[CH:13][NH:12][C:11]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 18616331methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 57756905methyl 3-(4-aminophenyl)-1H-pyrrole-2-carboxylateAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 0.1 g (0.942 mmol) of 10% palladium-on-charcoal in 35 cm3 of methanol is added, at a temperature in the region of 20° C., 1 g (4.061 mmol) of methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate. After hydrogenating for 20 hours in an autoclave under 3 bar of hydrogen, at a temperature in the region of 35° C., the reaction mixture is filtered, the catalyst is rinsed with twice 5 cm3 of methanol and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) to give 0.67 g of methyl 3-(4-aminophenyl)-1H-pyrrole-2-carboxylate in the form of an orange-coloured solid; M.W.=216, IE: m/z=216 M+, m/z=184 [M-CH3OH]+, m/z=155 [M−H2COOCH3]+.

Aufarbeitung

  1. filtrationthe reaction mixture is filtered
  2. washthe catalyst is rinsed with twice 5 cm3 of methanol
  3. concentrationthe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-c67f36321ae247e397c4b81902690b58
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560571B2

Verknüpfte Notizen

Wird geladen…