2-Hydrazinopyridine → HCID 178515966, compound

HRID 476203

Reaction equation

HRID 476203 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].C([O:11][C:12](=O)[CH2:13][C:14](=O)/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C>C(O)(=O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[N:1]1[C:12]([OH:11])=[CH:13][C:14]([CH:15]=[CH:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:2]1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 11053129Ethyl-3-oxo-5-phenylpent-4-enoate

Product 1

HCID 178515966HCID 178515966, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

2-hydrazinopyridine (161 mg, 1.477 mmol) was added to a solution of (E)-ethyl-5-phenyl-3-oxopent-4-enoate (8a, 355 mg, 1.62 mmol) prepared in Example C-1 in acetic acid (3 mL), followed by stirring under reflux at 60° C. for 30 minutes. Then, the reaction solution was concentrated by distillation under reduced pressure, and ethyl acetate (5 mL) and water (5 mL) were added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and separated by column chromatography (n-Hex/EtOAc=10/1 (v/v)) to afford the title compound.

Workup

  1. concentrationThen, the reaction solution was concentrated by distillation under reduced pressure, and ethyl acetate (5 mL) and water (5 mL)
  2. additionwere added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customseparated by column chromatography (n-Hex/EtOAc=10/1 (v/v))

Sources & evidence

ORD record
ord-039573d07fb6453ebedaca2359e2394d
Source dataset
uspto-grants-2014_01
Patent number
US08637674B2

Linked notes

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