Sodium Hydroxide → HCID 86690482, compound

HRID 1026756Notes

Reaction equation

HRID 1026756 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH2:22][CH2:23][CH3:24])=O)[CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>O1CCCC1>[C:7]1([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH2:19][NH:21][CH2:22][CH2:23][CH3:24])[CH:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86690480HCID 86690480, compound

Product 1

HCID 86690482HCID 86690482, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride was added to a solution of 4-phenyl-N-propylpyridine-2-carboxamide (350 mg) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 1 hr, followed by stirring with heating at 70° C. for 2 hr. After the mixture was cooled in ice, 10% aqueous sodium hydroxide solution was added, and the resulting mixture was stirred at room temperature for 30 min. The reaction mixture was dried over anhydrous magnesium sulfate, the desiccant was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=50:50-0:100) to afford the title compound (107 mg).

Workup

  1. stirringby stirring
  2. temperaturewith heating at 70° C. for 2 hr
  3. temperatureAfter the mixture was cooled in ice
  4. stirringthe resulting mixture was stirred at room temperature for 30 min
  5. dry with materialThe reaction mixture was dried over anhydrous magnesium sulfate
  6. filtrationthe desiccant was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=50:50-0:100)

Sources & evidence

ORD record
ord-d2aea84e2dce4cf48cf074d08a1b924f
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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