Hydrazine hydrate (1:1) → 5-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide
Reaction equation
[C:1]([C:3](=[C:7](SC)[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[C:4]([NH2:6])=[O:5])#[N:2].O.[NH2:21][NH2:22]>C(O)C>[NH2:2][C:1]1[NH:22][N:21]=[C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[C:3]=1[C:4]([NH2:6])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
2-cyano-3-(methylthio)-3-((4-nitrophenyl)amino)acrylamide was then suspended in 100 mL of ethanol and hydrazine hydrate (5.153 mL, 2.00 eq.) was added drop wise to the reaction. The reaction was then heated at 75° C. until the starting material was no longer present as confirmed via HPLC. Once starting material was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide as an off white to yellow powder as product. Product was allowed to dry under vacuum for 1 hr.
Workup
- customwise to the reaction
- custom(18 hrs), reaction
- customwas brought to room temperature
- filtrationfiltered
Sources & evidence
- ORD record
- ord-5c7ca40cfeeb43deb3835af53da5d097
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346792B2
Reaction notes
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