HCID 14450249, compound → HCID 14450270, compound

HRID 1199525Notes

Reaction equation

HRID 1199525 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. (4.13×105Pa) 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 waschromatographed 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. washeluting with methanol
  11. customCombination and evaporation of the appropriate fractions
  12. customafforded a solid which
  13. customwas recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1b6724d283bc413597f4be7445bfbd02
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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