6-phenylnicotinic acid N'-(4-methoxybutyryl)hydrazide → 5-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine

HRID 6927

Reaction equation

HRID 6927 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][NH:9][C:10](=[O:23])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:13][CH:12]=1)=O>P(Cl)(Cl)(Cl)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[O:23][C:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:13][CH:12]=2)=[N:9][N:8]=1

Participants

3

Reactant 1

HCID 695844476-phenylnicotinic acid N'-(4-methoxybutyryl)hydrazide

Product 1

HCID 220192365-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridineYield 65.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
100 °C

Procedure

To 6-phenylnicotinic acid N′-(4-methoxybutyryl)hydrazide (6.06 g) was added phosphorus oxychloride (100 ml), and stirred at 100° C. for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was concentrated under reduced pressure. To the resulting residue was added aqueous 1 mol/liter sodium hydroxide solution under ice cooling, and extracted with chloroform. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1 to 1/1 to 1/2 to 1/5), and washed with a mixture solvent of n-hexane and ethyl acetate, to afford the entitled compound 5-[5-(3-methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine 3.72 g, 65%). The physico-chemicalvalues are as follows.

Workup

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. concentrationthe solution was concentrated under reduced pressure
  3. additionTo the resulting residue was added aqueous 1 mol/liter sodium hydroxide solution under ice cooling
  4. extractionextracted with chloroform
  5. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1 to 1/1 to 1/2 to 1/5)
  8. washwashed with a mixture solvent of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-27aad1f22981490b815940bdd6106842
Source dataset
uspto-grants-2006_08
Patent number
US07084164B2

Linked notes

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