Sodium Hydroxide → HCID 86683166, compound

HRID 920948Notes

Reaction equation

HRID 920948 reaction equation
C([NH:4]/[N:5]=[CH:6]/[C:7]1[CH:17]=[N:16][CH:15]=[C:14]([Cl:18])[C:8]=1[C:9](OCC)=[O:10])(=O)C.[OH-].[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1>[Cl:18][C:14]1[C:8]2[C:9](=[O:10])[NH:4][N:5]=[CH:6][C:7]=2[CH:17]=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 140606546HCID 140606546, compound

Product 1

HCID 86683166HCID 86683166, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(E)-ethyl 3-((2-acetylhydrazono)methyl)-5-chloroisonicotinate (220 mg, 0.816 mmol) and aq. NaOH solution (3.26 mg, 0.082 mmol, 2 molar) in 5 mL of dioxane were stirred in a microwave at 165° C. for 60 min. Then the reaction mixture was basified by addition of aq. NaHCO3 and extracted with DCM. The organic phase was washed with brine, dried and concentrated. The crude title compound was purified by chromatography (eluent: DCM/methanol) to give 25 mg (16.88%) of the title compound as beige solid.

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude title compound was purified by chromatography (eluent: DCM/methanol)

Sources & evidence

ORD record
ord-c902341448284337a4735ac2bbe08a13
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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