Water → 1-(2-chlorophenyl)-3-(methoxycarbonyl)-1H-pyrazole-5-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[O:14]C=CC=2)=[CH:11][C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:9]1.O.C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:29].[Na+]>C(#N)C.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([OH:14])=[O:29])=[CH:11][C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:9]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred mixture of compound 6 (3.0 g, 9.9 mmol) in a mixture of acetonitrile (60 mL), water (80 mL) and carbon tetrachloride (60 mL) was added sodium periodate (8.3 g, 39 mmol) and ruthenium chloride (125 mg, 0.03 mmol) and the reaction mixture was stirred at room temperature for 72 h. On completion, solvent was removed, crude mass was dissolved in saturated sodium bicarbonate solution, extracted with ether (50 ml×3). Aqueous layer was acidified with 1N HCl and extracted with ethyl acetate (60 mL×4). The combined ethyl acetate layer was washed with brine, dried over sodium sulphate and concentrated to afford the title compound 7 (1.2 g, 44%) which was used for further reaction.
Workup
- customOn completion, solvent was removed
- dissolutioncrude mass was dissolved in saturated sodium bicarbonate solution
- extractionextracted with ether (50 ml×3)
- extractionextracted with ethyl acetate (60 mL×4)
- washThe combined ethyl acetate layer was washed with brine
- dry with materialdried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bb4fe09bf2744ca0b67aa3fc6d2d3437
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987318B2
Reaction notes
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