Potassium Sodium Tartrate → Methyl 5-amino-1-methyl-1h-indole-2-carboxylate
Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][CH:8]=2)=[O:4].O.O.Cl[Sn]Cl.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([NH2:14])=[CH:9][CH:8]=2)=[O:4]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
1-Methyl-5-nitro-1H-indole-2-carboxylic acid methyl ester (70 mg, 0.3 mmol) was dissolved in DMF (5 ml) and SnCl2.2H2O (339 mg, 1.5 mmol) was added as a solid. The resulting solution was stirred at 60° C. for 4 h. After cooling to room temperature, a pre-mixed aqueous solution of saturated Rochelle's salt (3 ml) and saturated NaHCO3 (3 ml) was added to the reaction mixture and the aqueous layer was extracted with EtOAc (3×6 ml). The organic layer was washed with H2O (3 ml), 1:1 NaHCO3: Rochelle's salt solution (3 ml), dried (MgSO4), filtered and the solvent was removed in vacuo to give the title compound.
Aufarbeitung
- temperatureAfter cooling to room temperature
- extractionthe aqueous layer was extracted with EtOAc (3×6 ml)
- washThe organic layer was washed with H2O (3 ml), 1:1 NaHCO3
- dry with materialRochelle's salt solution (3 ml), dried (MgSO4)
- filtrationfiltered
- customthe solvent was removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-1204bfb4b7bd4c7288a8274ee7029191
- Quelldatensatz
- uspto-grants-2010_09
- Patentnummer
- US07803841B2
Notizen zur Reaktion
Wird geladen…