HCID 22624532, compound → HCID 22624530, compound

HRID 1636682Notes

Reaction equation

HRID 1636682 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[CH:18][CH:17]=3)[CH:12]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[N:13]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]([F:28])([F:29])[CH:25]([F:26])[F:27])=[CH:20][CH:21]=3)[CH:12]=[N:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 22624532HCID 22624532, compound

Product 1

HCID 22624530HCID 22624530, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-(4-Nitrophenyl)-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (5.5 g) and 10% palladium-carbon (50% wet, 0.5 g) were added to methanol (200 ml). The mixture was subjected to catalytic hydrogenation at ordinary temperature under ordinary pressure. When hydrogen absorption stopped, dichloromethane (200 ml) was added thereto and the catalyst was removed by filtration. The catalyst was washed with dichloroethane (50 ml). The washings and the filtrate were combined and distilled under reduced pressure to give 2-(4-aminophenyl)-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (4.6 g, 90%) as a white solid. This compound was used for the next process without purification.

Workup

  1. customWhen hydrogen absorption
  2. additiondichloromethane (200 ml) was added
  3. customthe catalyst was removed by filtration
  4. washThe catalyst was washed with dichloroethane (50 ml)
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-4da50a2bfa5c47ea92f727c595d6ee53
Source dataset
uspto-grants-2000_03
Patent number
US06034248

Reaction notes

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