Hydrochloric Acid → methyl 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylate
Reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]([C:13]#[C:14][C:15](OC)=[O:16])=[O:12].N1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C1COCC1.CCOC(C)=O>[O:16]=[C:15]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:8][C:13]([C:11]([O:10][CH3:9])=[O:12])=[CH:14]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 67 °C
Procedure
Phenylhydrazine (0.5 g; 4.62 mmol), acetylenedicarboxylic acid dimethyl ester (0.66 g; 4.62 mmol) and 4-toluenesulfonic acid pyridine salt (1.16 g; 4.62 mmol) were dissolved in 7 ml of dry THF under nitrogen atmosphere and the solution was stirred for 2 h at RT after which 7 ml of 10% HCl (g) in EtOAc was added and the mixture heated at 67° C. for 5 h. The reaction mixture evaporated to dryness and 6 ml of DCM added to the residue. The organic phase was washed with 8 ml of water and the combined water phases were extracted with 2×6 ml of DCM. The combined organic phases were once more washed with 12 ml of water, dried over Na2SO4, filtered and evaporated to dryness to give 0.35 g of the product which was used as such without further purification.
Workup
- additionwas added
- customThe reaction mixture evaporated to dryness and 6 ml of DCM
- additionadded to the residue
- washThe organic phase was washed with 8 ml of water
- extractionthe combined water phases were extracted with 2×6 ml of DCM
- washThe combined organic phases were once more washed with 12 ml of water
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-2acae527acaa453ab559e9768bdadc8e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
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