2-Hydrazinopyridine → HCID 178516273, compound

HRID 476201Notes

Reaction equation

HRID 476201 reaction equation
O=[C:2]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6]CC)=O.[NH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[NH2:18]>C(O)C>[O:10]([CH2:9][C:2]1[CH:3]=[C:4]([OH:6])[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 3016246Ethyl 3-oxo-4-phenoxybutyrate

Product 1

HCID 178516273HCID 178516273, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl 3-oxo-4-phenoxybutanoate (5a, 1.2 g, 5.4 mmol) was charged in a 25 mL round-bottom flask and dissolved in 10 mL of ethanol. A solution of 2-hydrazinopyridine (0.55 g, 5.0 mmol) in 5 mL of ethanol at 100° C. was gradually added thereto over 30 minutes, followed by stirring for 20 hours. After completion of the reaction was confirmed by TLC, the reaction solution was concentrated by evaporation, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and then purified by column chromatography (n-Hex/EtOAc=9/1 (v/v)) to afford the title compound.

Workup

  1. concentrationthe reaction solution was concentrated by evaporation
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (n-Hex/EtOAc=9/1 (v/v))

Sources & evidence

ORD record
ord-17c8f743babe42f389e89c9fd206f938
Source dataset
uspto-grants-2014_01
Patent number
US08637674B2

Reaction notes

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