Methanol → 4-amino-3-(propan-2-yl)-1H-pyrazole-5-carboxamide

HRID 19587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19587
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH2:11])=[O:10])[C:5]=1[N+:12]([O-])=O)([CH3:3])[CH3:2].CO>[Ni].O>[NH2:12][C:5]1[C:6]([C:9]([NH2:11])=[O:10])=[N:7][NH:8][C:4]=1[CH:1]([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 887MethanolHCID 160997461H-Pyrazole-3-carboxamide, 5-(1-methylethyl)-4-nitro-

Produkt 1

HCID 160997494-amino-3-(propan-2-yl)-1H-pyrazole-5-carboxamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 5-isopropyl-4-nitropyrazol-3-carboxamide (2.57 g; 12.97 mmol), methanol (20 mL) and water (5 mL) was added 0.7 g Raney Ni (W5). The mixture was stirred under hydrogen atmosphere (760 torr) for four hours. The reaction mixture was filtered, the filtrate was concentrated to dryness in vacuo and the residue was recrystallized from ethyl acetate to yield 1.94 g (89%) of the product. The product was purified by chromatography on silica gel, the mixture of chloroform/methanol (97/3) was used as mobile phase. Yield 95%; mp=178-179° C.; MS (ES+): 169.1 (100%, M+H+). 1H NMR (CD3OD; 400 MHz): 1.31 d (6H; J=7.5 Hz), 3.06 sept (1H; J=7.5 Hz), 4.83 s (2H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness in vacuo
  3. customthe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ced9d1d51268491a831fde3de0687dce
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745450B2

Notizen zur Reaktion

Wird geladen…