Acetic Acid → N-[4-(1-methylethoxy)phenyl]-1H-pyrazol-5-amine
Reaction equation
C([N:8]1[C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=[CH:11][CH:10]=[N:9]1)C1C=CC=CC=1.C(O)(=O)C.C([O-])=O.[NH4+].C(OCC)(=O)C>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:23][CH:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:12]2[NH:8][N:9]=[CH:10][CH:11]=2)=[CH:19][CH:18]=1)[CH3:22]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of 1-benzyl-N-[4-(1-methylethoxy)phenyl]-1H-pyrazol-5-amine (0.80 g) and palladium hydroxide (10 wt %, 0.80 g) in ethanol (4.5 mL)-acetic acid (0.5 mL) was added ammonium formate (0.49 g) at 80° C. After stirring at 80° C. for 2 hr, the mixture was allowed to cool, ethyl acetate was added, and the insoluble material was filtered off. Saturated aqueous sodium hydrogen carbonate solution was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.37 g, 66%).
Workup
- temperatureto cool
- filtrationthe insoluble material was filtered off
- additionSaturated aqueous sodium hydrogen carbonate solution was added to the filtrate
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-1be4d459d452435b86cc8b51184f6a16
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115136B2
Reaction notes
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