Water → 1-(1-Amino-1H-pyrrol-2-yl)ethanone

HRID 1451977

Reaktionsgleichung

Reaktionsgleichung von HRID 1451977
[C:1]([C:4]1[N:5]([N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].CN.O>CN(C)C=O>[NH2:9][N:5]1[CH:6]=[CH:7][CH:8]=[C:4]1[C:1](=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6329MethylamineHCID 199667522-(2-Acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

Produkt 1

HCID 199667441-(1-Amino-1H-pyrrol-2-yl)ethanoneAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 2-(2-acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (8.53 g) in dimethylformamide (25 ml) was added 33 ml of 40% methylamine solution. After 2.5 hours, the reaction mixture was poured into water (300 ml) and was extracted 4 times with EtOAc. The combined organics were washed once with water and brine, dried (MgSO4), filtered and concentrated to give the crude product. Purification via flash column chromatography (silica gel, 30% EtOAc/hexane) afforded 3.88 g of the product as an oil.

Aufarbeitung

  1. extractionwas extracted 4 times with EtOAc
  2. washThe combined organics were washed once with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification via flash column chromatography (silica gel, 30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b14709ea61d846a78180e562f3dadce8
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05605925

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