HCID 14450249, compound → HCID 14450270, compound

HRID 1904366Notes

Reaction equation

HRID 1904366 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:15]=[N:14][N:13]=[CH:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(O)(=O)C.[Ni]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:12]=[N:13][N:14]=[CH:15]2)=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 14450249HCID 14450249, compound

Product 1

HCID 14450270HCID 14450270, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-(3-methyl-4-nitrophenyl)-1,2,4-triazole (1.0 g) in acetic acid (25 cm3) was hydrogenated at 25° and 60 p.s.i. (4.13×1015Pa) pressure over Raney nickel (0.2 g) for 2 hours. The mixture was then filtered through "Solkafloc" (Trade Mark for a cellulose based filtering agent), the solvent was evaporated in vacuo and the residue was partitioned between chloroform (100 cm3) and aqueous sodium carbonate solution (20 cm3). The aqueous phase was further extracted with chloroform (3×50 cm3) and the combined and dried (MgSO4) organic extracts were concentrated to afford an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:ethyl acetate, 1:9. Combination and evaporation of the appropriate fractions afforded a solid which was recrystallised from ethyl acetate/hexane to give 4-(4-amino-3-methylphenyl)-1,2,4-triazole, m.p. 152°-154° (0.67 g).

Workup

  1. customwas hydrogenated at 25°
  2. filtrationThe mixture was then filtered through "Solkafloc" (Trade Mark for a cellulose
  3. filtrationbased filtering agent), the solvent
  4. customwas evaporated in vacuo
  5. customthe residue was partitioned between chloroform (100 cm3) and aqueous sodium carbonate solution (20 cm3)
  6. extractionThe aqueous phase was further extracted with chloroform (3×50 cm3)
  7. dry with materialdried (MgSO4) organic extracts
  8. concentrationwere concentrated
  9. customto afford an oil which
  10. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  11. washeluting with methanol
  12. customCombination and evaporation of the appropriate fractions
  13. customafforded a solid which
  14. customwas recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-befb41964e5249b9bcdb3392da74c525
Source dataset
uspto-grants-1989_06
Patent number
US04837334

Reaction notes

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