Sodium Hydroxide → HCID 57808368, compound

HRID 1043689Notes

Reaction equation

HRID 1043689 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][N:5]=1)[NH2:3].[C:11]([CH2:14][C:15](=O)[CH3:16])(=O)[CH3:12].[OH-].[Na+]>O>[CH3:10][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([N:2]2[C:15]([CH3:16])=[CH:14][C:11]([CH3:12])=[N:3]2)[CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31261AcetylacetoneHCID 66858765HCID 66858765, compound

Product 1

HCID 57808368HCID 57808368, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 50 mL recovery flask, 2-hydrazino-4-methylpyridine hydrochloride (0.5 g, 3.13 mmol), acetylacetone (0.376 g, 3.76 mmol), and water (7 mL) were added and stirred at room temperature for 16 hours. Upon completion of the reaction, a 10% aqueous solution of sodium hydroxide was added to the reaction mixture to adjust the pH up to 14. The resulting mixture was extracted with ethyl acetate twice, and the organic phases were combined and washed with saturated brine once, and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 0.47 g of the title compound (yield 80%).

Workup

  1. customUpon completion of the reaction
  2. extractionThe resulting mixture was extracted with ethyl acetate twice
  3. washwashed with saturated brine once
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-09f68b4c21ba4653870c5b0f60ce6e7e
Source dataset
uspto-grants-2013_10
Patent number
US08563552B2

Reaction notes

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