HCID 2763461, compound → 4-(5-butyl-1,3,4-oxadiazol-2-yl)aniline

HRID 979278Notes

Reaction equation

HRID 979278 reaction equation
[CH2:1]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[N:8][N:9]=1)[CH2:2][CH2:3][CH3:4]>[Ni].C(O)(=O)C>[CH2:1]([C:5]1[O:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[N:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 2763461HCID 2763461, compound

Product 1

HCID 27634654-(5-butyl-1,3,4-oxadiazol-2-yl)anilineYield 74%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 24.7 parts of 2-butyl-5-(p-nitrophenyl)-1,3,4-oxadiazole, 2.5 parts of an aqueous Raney nickel suspension and 250 parts of glacial acetic acid is hydrogenated at room temperature, while shaking. When the absorption of hydrogen is complete, 2.5 parts of active carbon are added, the mixture is filtered, the filtrate is poured into saturated aqueous sodium chloride solution, and the resulting precipitate is filtered off under suction, washed with water and dried. 16 parts (74% of theory) of 2-butyl-5-(p-aminophenyl)-1,3,4-oxadiazole of melting point 125° C. (toluene) are obtained.

Workup

  1. customis hydrogenated at room temperature
  2. customWhen the absorption of hydrogen
  3. addition2.5 parts of active carbon are added
  4. filtrationthe mixture is filtered
  5. additionthe filtrate is poured into saturated aqueous sodium chloride solution
  6. filtrationthe resulting precipitate is filtered off under suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f4ba462c516e43768fd0667a23e42f1d
Source dataset
uspto-grants-1987_05
Patent number
US04667020

Reaction notes

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