Hydrochloric Acid → 4-Nitroso-1-(2-pyridinyl)-1H-pyrazol-5-amine
Reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([NH2:13])=[CH:11][CH:10]=[N:9]1.[N:14](OCCC(C)C)=[O:15]>C(O)C>[N:14]([C:11]1[CH:10]=[N:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[C:12]=1[NH2:13])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
HCl (37%, 11 μl) was added to a heterogeneous solution of 2-pyridin-2-yl-2H-pyrazol-3-ylamine (2.2 g, 13.7 mmol) in absolute ethanol (15 ml). The reaction mixture was subsequently cooled to 0° C. and isopentyl nitrite (2.02 ml, 15 mmol) was slowly added. The reaction mixture became dark. After the isopentyl nitrite had been completely added, the reaction mixture was allowed to return to ambient temperature. After 2.5 h at ambient temperature, the reaction mixture was cooled to 5° C. and filtered. The solid was washed with absolute MeOH (10 ml) and was then triturated twice from heptane. The solid was dried under vacuum at 35° C. to give 4-nitroso-2-pyridin-2-yl-2H-pyrazol-3-ylamine (2.1 g, 81%) in the form of a green solid.
Workup
- customto return to ambient temperature
- temperaturethe reaction mixture was cooled to 5° C.
- filtrationfiltered
- washThe solid was washed with absolute MeOH (10 ml)
- customwas then triturated twice from heptane
- customThe solid was dried under vacuum at 35° C.
Sources & evidence
- ORD record
- ord-1b832a5b128d49a0aedae36d2786d730
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07056354B2
Reaction notes
Loading…