2-Hydrazinopyridine → HCID 178438380, compound

HRID 1467958Notes

Reaction equation

HRID 1467958 reaction equation
[C:1]([CH:9]([CH2:15][CH2:16][CH3:17])[C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[NH2:19]>C(O)C>[C:2]1([C:1]2[C:9]([CH2:15][CH2:16][CH3:17])=[C:10]([OH:12])[N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:19]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 251321ethyl 2-benzoylpentanoate

Product 1

HCID 178438380HCID 178438380, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-benzoylpentanoate (355 mg, 1.5 mmol) was dissolved in 5 mL of ethanol to which 2-hydrazinopyridine (163 mg, 1.5 mmol) was then added, followed by refluxing at 100° C. After 20 hours, ethanol was concentrated, followed by extraction with ethyl acetate. The extract was washed two or three times with water, and the organic layer was dried over anhydrous MgSO4 and then concentrated. The resulting residue was purified by column chromatography (n-hexane:EA=10:1) to afford the title compound.

Workup

  1. additionwas then added
  2. concentrationethanol was concentrated
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed two or three times with water
  5. dry with materialthe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (n-hexane:EA=10:1)

Sources & evidence

ORD record
ord-9e16357e02c14b4ba5a77b81920e7a43
Source dataset
uspto-grants-2015_04
Patent number
US09000176B2

Reaction notes

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