1-[2-Fluoro-4-chloro-5-(4-nitrophenoxy)phenyl]-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-one → 1-[5-(4-aminophenoxy)-4-chloro-2-fluorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one

HRID 1090979Notes

Reaction equation

HRID 1090979 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[CH:6][C:5]([N:18]2[C:22](=[O:23])[N:21]([CH:24]([F:26])[F:25])[C:20]([CH3:27])=[N:19]2)=[C:4]([F:28])[CH:3]=1>C(O)C.[Pt]=O>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:7]2[C:2]([Cl:1])=[CH:3][C:4]([F:28])=[C:5]([N:18]3[C:22](=[O:23])[N:21]([CH:24]([F:26])[F:25])[C:20]([CH3:27])=[N:19]3)[CH:6]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 199122141-[2-Fluoro-4-chloro-5-(4-nitrophenoxy)phenyl]-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 199122101-[5-(4-aminophenoxy)-4-chloro-2-fluorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-oneYield 79.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Hydrogenation of 5.80 g (0.015 mole) of 1-[4-chloro-2-fluoro-5-(4-nitrophenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one dissolved in 100 mL of ethanol in the presence of a catalytic amount (0.30 g) of platinum oxide produced 4.6 g of 1-[5-(4-aminophenoxy)-4-chloro-2-fluorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid, m.p. 133°-135° C., Compound 3 of Table 1.

Sources & evidence

ORD record
ord-8ef887ef4c5f40dbb390d1966feb7bd0
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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