Hydrogen Peroxide → HCID 57748585, Verbindung

HRID 906186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906186
[C:1]([C:3]1[C:11]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[C:5]([CH3:18])[N:4]=1)#[N:2].OO.C(=O)([O-])[O-:22].[K+].[K+].[OH-].[K+]>CS(C)=O.O.CO>[NH2:2][C:1]([C:3]1[C:11]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:18])[N:4]=1)=[O:22]

Komponenten

8

Edukt 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 86631952HCID 86631952, Verbindung

Produkt 1

HCID 57748585HCID 57748585, VerbindungAusbeute 348,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6-cyano-2-methyl-5-(pentan-3-ylamino)nicotinate (0.543 g, 1.97 mmol) in DMSO (10 ml) were added 50% aqueous hydrogen peroxide (0.2441 g, 3.55 mmol) and potassium carbonate (0.068 g, 0.49 mmol) at 10° C. The reaction mixture was stirred at room temperature for two hours then a solution of potassium hydroxide (0.22 g, 3.94 mmol) in water (2 ml) and methanol (10 ml) were added to above reaction mixture. After being stirred for another two hours at 45° C., the reaction mixture was cooled to room temperature and neutralized to PH 7. 6-(Aminocarbonyl)-2-methyl-5-(pentan-3-ylamino)nicotinic acid (0.453 g, 87%) was obtained by filtration and drying. 1HNMR (400 MHz, MeOH-D4): 7.62 (s, 1H), 3.35 (m, 1H), 2.60 (s, 3H), 1.65 (m, 2H), 1.52 (m, 2H), 0.95 (t, J=7.20 Hz, 6H). MS (EI) for C13H20N3O3: 267.2 (MH+).

Aufarbeitung

  1. stirringAfter being stirred for another two hours at 45° C.
  2. temperaturethe reaction mixture was cooled to room temperature and neutralized to PH 7

Quellen und Nachweise

ORD-Eintrag
ord-2516f0e326bd4ca9b75607537671dbe7
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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