Reaktion #48576

Reaktionsgleichung

4-nitro-3-pyrazolecarboxylic acid

trans 4-aminocyclohexanol

EDAC

HOBt

→

4-nitro-1H-pyrazole-3-carboxylic acid 4-hydroxy-cyclohexylamide

Ausbeute 24.2%

Lösungsmittel

CH2Cl2

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed successively with 5% citric acid, saturated aqueous sodium bicarbonate, water and brine
2. 2
   Waschenwash
3. 3
   Extraktionextracted with EtOAc
4. 4
   TrocknenThe organic layer was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give a white solid, which
8. 8
   Sonstigewas triturated with CHCl3

Vorschrift

A mixture of 4-nitro-3-pyrazolecarboxylic acid (4.98 g, 31.7 mmol), trans 4-aminocyclohexanol (3.65 g, 31.7 mmol), EDAC (6.68 g, 34.8 mmol) and HOBt (4.7 g, 34.8 mmol) in DMF (120 ml) was stirred at ambient temperature for 16 hours. The mixture was reduced in vacuo, the residue taken up in CH2Cl2 and washed successively with 5% citric acid, saturated aqueous sodium bicarbonate, water and brine. The product was found to be mainly in the citric acid wash, which was basified and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to give a white solid, which was triturated with CHCl3 to give 1.95 g of 4-nitro-1H-pyrazole-3-carboxylic acid 4-hydroxy-cyclohexylamide. (LC/MS: Rt 1.62, [M+H]+ 255).

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