Potassium Carbonate → N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide

HRID 384261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384261
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13].[H-].[Na+].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:3]([NH:11][C:12](=[O:14])[CH3:13])[CH:4]=1)([O-:10])=[O:9]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 3292867Acetamide, N-(2-hydroxy-5-nitrophenyl)-

Produkt 1

HCID 58098809N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of N-(2-hydroxy-5-nitrophenyl)acetamide (870 mg, 4.44 mmol) in DMF (5 mL) was added NaH (196 mg, 5.32 mmol) and K2CO3 (2.11 g, 13.32 mmol), followed by 1-(2-chloroethyl)pyrrolidine hydrochloride (905 mg, 5.32 mmol). After heating at 100° C. for 20 h, the solution was poured to ice, and was extracted with EtOAc, organic layer was washed with Sat. NaHCO3, brine, dried and concentrated to give N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide (430 mg).

Aufarbeitung

  1. additionthe solution was poured to ice
  2. extractionwas extracted with EtOAc, organic layer
  3. washwas washed with Sat. NaHCO3, brine
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-182f0f1697c64ecc978d4050f6b5f349
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367689B2

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