HCID 12877070, compound → HCID 20434239, compound

HRID 1154738Notes

Reaction equation

HRID 1154738 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH2:16][CH2:17][CH3:18])=[N:14][CH:13]=[N:12]2)=[CH:7][CH:6]=1)([O-])=O.[H][H]>[Pd].CO>[ClH:1].[ClH:1].[CH2:16]([C:15]1[N:11]([C:8]2[CH:7]=[CH:6][C:5]([NH2:2])=[CH:10][CH:9]=2)[N:12]=[CH:13][N:14]=1)[CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 12877070HCID 12877070, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20434239HCID 20434239, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 38.3 parts of 1-(4-nitrophenyl)-5-propyl-1H-1,2,4-triazole monohydrochloride and 400 parts of methanol is hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is dissolved in water and neutralized with sodium hydrogen carbonate. The product is extracted with dichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanol. The salt is filtered off and dried, yielding 35 parts (91%) of 4-(5-propyl-1H-1,2,4-triazol-1-yl)benzenamine dihydrochloride.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in water and neutralized with sodium hydrogen carbonate
  4. extractionThe product is extracted with dichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe salt is filtered off
  10. customdried

Sources & evidence

ORD record
ord-84158457ee8645a292288ca34758712a
Source dataset
uspto-grants-1984_12
Patent number
US04490530

Reaction notes

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