Sodium Chloride → 5-Nitro-1H-indole-2-carboxylic acid propylamide

HRID 450719

Reaktionsgleichung

Reaktionsgleichung von HRID 450719
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([OH:15])=O)=[CH:7]2)([O-:3])=[O:2].[CH2:16]([NH2:19])[CH2:17][CH3:18].[Cl-].[Na+]>CN(C)C=O.O>[CH2:16]([NH:19][C:13]([C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)=[O:15])[CH2:17][CH3:18]

Komponenten

6

Edukt 3

HCID 5234Sodium ChlorideHCID 7852PropylamineHCID 3512915-Nitroindole-2-carboxylic acid

Produkt 1

HCID 670239755-Nitro-1H-indole-2-carboxylic acid propylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-nitro-1H-indole-2-carboxylic acid (6.95 g, 33.7 mmol) in N,N-dimethylformamide (DMF)/pyridine (1/1, 150 ml) N,N′-carbonyl-diimidazole (5.47 g, 33.71 mmol) was added. The mixture was stirred at 80° C. for 1 h. At 0° C. propylamine (9.96 g, 168.56 mmol) was added. The mixture was stirred at 0° C. for 1 h and then at room temperature for 16 h. The solution was diluted with water (2 I). After addition of sodium chloride the product precipitated. After filtration the residue was washed with water and pentane, and dried in a vacuum oven at 50° C. to give the product as a yellow powder.

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. waitat room temperature for 16 h
  3. customprecipitated
  4. filtrationAfter filtration the residue
  5. washwas washed with water and pentane
  6. customdried in a vacuum oven at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-1e80d39d99c34aa49004d959ce0d27c2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486984B2

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