Water → HCID 59411398, Verbindung

To a solution of ethyl 4-nitro-1H-pyrrol-2-carboxylate (10 g) in N,N-dimethylformamide (100 mL) was slowly added sodium hydride (60%, oily, 2.4 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Ethyl iodide (4.8 mL) was slowly added to the reaction mixture, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. A mixture of the residue and 10% palladium-carbon (50% containing water, 1.0 g) in tetrahydrofuran (20 mL)-ethanol (20 mL) was stirred at room temperature for 12 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give ethyl 4- amino-1-ethyl-1H-pyrrole-2-carboxylate (7.1 g, yield 78%) as a brown oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

1. customat 0° C.
2. stirringthe mixture was stirred at room temperature overnight
3. extractionthe mixture was extracted with ethyl acetate
4. washThe ethyl acetate layer was washed with saturated brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. additionA mixture of the residue and 10% palladium-carbon (50% containing water, 1.0 g) in tetrahydrofuran (20 mL)-ethanol (20 mL)
8. stirringwas stirred at room temperature for 12 hr under a hydrogen atmosphere
9. filtrationThe catalyst was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-b3fe4e2f516c40a78d213dae41027908

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08492405B2