Hydrochloric Acid → HCID 59214340, compound
Reaction equation
[H-].[Li+].[CH3:3][O:4][C:5]([C:7]1[CH:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=1)=[O:6].I[CH2:15][CH:16]([CH3:18])[CH3:17].Cl>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9](=[O:13])[CH:8]=1)=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
LiH (78 mg) was suspended in DMF (5 ml), and a suspension of methyl-2-oxo-1,2-dihydropyridine-4-carboxylate (500 mg) in DMF (5 ml) was added dropwise thereto at room temperature. The suspension was stirred as it was, and a solution of 1-iodo-2-methylpropane (506 μl) in DMF (5 ml) was added dropwise thereto over 10 min, followed by stirring at 50° C. for 15 hours. To the reaction solution was added 1M HCl at 0° C., followed by extraction with EtOAc, and the organic layer was washed with saturated brine, dried over anhydrous MgSO4, and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:EtOAc=90:10 to 50:50) to obtain methyl-1-isobutyl-2-oxo-1,2-dihydropyridine-4-carboxylate (440 mg) as white powders.
Workup
- additionwas added dropwise
- customat room temperature
- stirringby stirring at 50° C. for 15 hours
- extractionfollowed by extraction with EtOAc
- washthe organic layer was washed with saturated brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel chromatography (n-hexane:EtOAc=90:10 to 50:50)
Sources & evidence
- ORD record
- ord-d07f8556e3f54dcfa47f49aeb45f1fed
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951825B2
Reaction notes
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