Hydrochloric Acid → HCID 59214340, compound

HRID 2244632Notes

Reaction equation

HRID 2244632 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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10556Isobutyl iodideHCID 62714Lithium hydrideHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 59214340HCID 59214340, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

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

  1. additionwas added dropwise
  2. customat room temperature
  3. stirringby stirring at 50° C. for 15 hours
  4. extractionfollowed by extraction with EtOAc
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (n-hexane:EtOAc=90:10 to 50:50)

Sources & evidence

ORD record
ord-7bf4e829e61742d380f8ad7e95b4f686
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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