Water → 1H-Pyrrole-2-carboxylic acid, 4-nitro-1-propyl-, ethyl ester

HRID 23156

Reaktionsgleichung

Reaktionsgleichung von HRID 23156
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2].[CH3:14][CH2:15][O-].[Na+].[CH3:18]I.O>CCO.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH2:15][CH3:14])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 242169Ethyl 4-Nitropyrrole-2-carboxylateHCID 2723922Sodium ethoxide

Produkt 1

HCID 9040721H-Pyrrole-2-carboxylic acid, 4-nitro-1-propyl-, ethyl esterAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Nitro-1H-pyrrole-2-carboxylic acid ethyl ester (5 g) was dissolved in 50 ml of dry EtOH, 50 ml of 1M sodium ethylate was added followed with 10 ml of CH3I. The reaction mixture was heated at 80° C. for 4 hours, cooled down to room temperature and distributed between water and chloroform. The organic phase was washed with water, dried with sodium sulfate and evaporated. The residue was recrystallized from hexane to yield 4.72 g (77%) of 1-propyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester 232. H1-NMR (DMSO-d6): 0.79 (t, 3H, CH3), 1.25 (t, 3H, CH3), 1.68 (m, 2H, CH2), 4.17-4.28 (m, 4H, 2CH2), 7.23 and 8.24 (d, 1H, pyrrole)

Aufarbeitung

  1. temperaturecooled down to room temperature
  2. washThe organic phase was washed with water
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-fd07c35c22c94de7a7c4d8b98aa27f07
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849713B2

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