Sodium Hydroxide → HCID 86683159, compound

HRID 920943Notes

Reaction equation

HRID 920943 reaction equation
C([NH:4]/[N:5]=[CH:6]/[C:7]1[N:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:8]=1[C:9](OCC)=[O:10])(=O)C.[OH-].[Na+]>O1CCOCC1>[Cl:18][C:14]1[C:8]2[C:9](=[O:10])[NH:4][N:5]=[CH:6][C:7]=2[N:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 140606545HCID 140606545, compound

Product 1

HCID 86683159HCID 86683159, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
145 °C

Procedure

(E)-ethyl 2-((2-acetylhydrazono)methyl)-4-chloronicotinate (2850 mg, 10.57 mmol) in 15 mL of dioxane was mixed with aq. NaOH (42.3 mg, 1.06 mmol, 2 M). The reaction mixture was stirred in a microwave for 60 min at 145° C. After cooling to room temperature, the solid was filtered off. The solid was dissolved in methanol and the residue was filtered off. The filtrate was concentrated and triturated with EA to give 1.4 g (73.0%) of the title compound as orange brown solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was filtered off
  3. dissolutionThe solid was dissolved in methanol
  4. filtrationthe residue was filtered off
  5. concentrationThe filtrate was concentrated
  6. customtriturated with EA

Sources & evidence

ORD record
ord-4356f439c9f24f35949c9328a5869843
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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