Reaction #1726705

ord-84fa9550a45b4384b436d713367932cc

Reaction equation

N#Cc1cnn(-c2cccc([N+](=O)[O-])c2)c1N
5-amino-1-(3′-nitrophenyl)-4-cyanopyrazole
O=P(O)(O)O
phosphoric acid
[NH4+].[OH-]
ammonium hydroxide
Nc1ccnn1-c1cccc([N+](=O)[O-])c1
5-amino-1-(3′-nitrophenyl)-pyrazole
Yield 80.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ExtractionThe organics were extracted three times with diethyl ether (total 40 ml)
  2. 2
    Washwashed with brine
  3. 3
    Dryingdried over magnesium sulfate
  4. 4
    OtherRemoval of solvent

Procedure

5-amino-1-(3′-nitrophenyl)-4-cyanopyrazole (559 mg, 2.44 mmol) and phosphoric acid (86%, 6 ml) were refluxed at 170° C. for 15 h. The reaction was cooled to room temperature and neutralized with ammonium hydroxide. The organics were extracted three times with diethyl ether (total 40 ml), washed with brine, and dried over magnesium sulfate. Removal of solvent gave 5-amino-1-(3′-nitrophenyl)-pyrazole as a yellow powder (398 mg, 80% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08110568B2uspto-grants-2012_02