2,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-one → 2-(4-aminophenyl)-2,4-dihydro-5-methyl-4-propyl-3H-1,2,4-triazol-3-one

HRID 2106761Notes

Reaction equation

HRID 2106761 reaction equation
[CH3:1][C:2]1[N:3]([CH2:17][CH2:18][CH3:19])[C:4](=[O:16])[N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[N:6]=1.[H][H]>[Pd].CO>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([N:5]2[C:4](=[O:16])[N:3]([CH2:17][CH2:18][CH3:19])[C:2]([CH3:1])=[N:6]2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 151254762,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 151254772-(4-aminophenyl)-2,4-dihydro-5-methyl-4-propyl-3H-1,2,4-triazol-3-oneYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 57 parts of 2,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-one and 400 parts of methanol was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 20%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product was filtered off and dried, yielding 46 parts (91%) of 2-(4-aminophenyl)-2,4-dihydro-5-methyl-4-propyl-3H-1,2,4-triazol-3-one, mp. 138.8° C. (int. 21).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-87cfc9b57d9c4d71938e65a05753d2fe
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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