Methanol → HCID 22624530, compound

HRID 279164Notes

Reaction equation

HRID 279164 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.CO.[H][H]>[C].[Pd].ClCCl>[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

6

Reactant 3

HCID 887MethanolHCID 22624532HCID 22624532, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22624530HCID 22624530, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolvent

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 absoption 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 next process without purification.

Workup

  1. customthe catalyst was removed by filtration
  2. washThe catalyst was washed with dichloroethane (50 ml)
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c0fd1219591b4ce891e3b0afd5f9991f
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

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