Hydrochloric Acid → 2-Methylpyrrole-3-carboxylic acid diethylamide

HRID 484007

Reaktionsgleichung

Reaktionsgleichung von HRID 484007
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[Al](C)C.C(O[C:13]([C:15]1[CH:19]=[CH:18][NH:17][C:16]=1[CH3:20])=[O:14])C.Cl>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([N:3]([CH2:4][CH3:5])[C:13]([C:15]1[CH:19]=[CH:18][NH:17][C:16]=1[CH3:20])=[O:14])[CH3:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylateHCID 16682925Trimethylaluminum

Produkt 1

HCID 217817222-Methylpyrrole-3-carboxylic acid diethylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 1.6 ml of diethylamine in 30 ml of toluene was added 7.5 ml of 2M trimethylaluminum in hexane, and the mixture stirred for 20 minutes. To this mixture was added 1.53 g of 2-methylpyrrole-3-carboxylic acid ethyl ester, and the reaction mixture refluxed overnight. The mixture was cooled, acidified with aqueous 2N hydrochloric acid and extracted twice with ethyl acetate and three times with methylene chloride. Solvent was removed from the combined extracts under reduced pressure, and the residue was flash chromatographed on silica gel, eluting with 75% ethyl acetate/hexane, giving 1.5 g of 2-methylpyrrole-3-carboxylic acid diethylamide, m.p. 120°-121° C., the compound of formula (b).

Aufarbeitung

  1. temperaturethe reaction mixture refluxed overnight
  2. temperatureThe mixture was cooled
  3. extractionextracted twice with ethyl acetate and three times with methylene chloride
  4. customSolvent was removed from the combined extracts under reduced pressure
  5. customchromatographed on silica gel
  6. washeluting with 75% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8836079c44b546d49aa5b5c85f70bce0
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229387

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