HCID 11099553, compound → 2-[[[1-(4-Chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]benzenamine

HRID 1828010Notes

Reaction equation

HRID 1828010 reaction equation
[H][H].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)=[N:11]2)=[CH:6][CH:5]=1>[Pt].C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH2:23])=[N:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 11099553HCID 11099553, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117485682-[[[1-(4-Chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]benzenamineYield 86.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

At 20-25° C. and a hydrogen pressure of 20 bar, a mixture of 30 g (90 mmol) of 2-[1-(4-chlorophenyl)pyrazol-3-yl]oxymethylnitrobenzene and 2 g of platinum on activated carbon (5%) in 200 ml of ethyl acetate was hydrogenated with stirring for approximately 20 hours. The mixture was filtered through Al2O3 and the solvent was removed from the filtrate by distillation, giving 23.3 g of the aniline as yellow crystals of m.p. 81-83° C.

Workup

  1. filtrationThe mixture was filtered through Al2O3
  2. customthe solvent was removed from the filtrate by distillation

Sources & evidence

ORD record
ord-21342ca281764f9f89ee5fbb21320313
Source dataset
uspto-grants-2006_06
Patent number
US07056941B1

Reaction notes

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