4,6-Dimethyl-2-(4-nitrophenoxy)pyrimidine → 4-((4,6-Dimethylpyrimidin-2-yl)oxy)aniline

HRID 1248892

Reaction equation

HRID 1248892 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[N:10]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>O1CCOCC1.[Ni]>[NH2:1][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[N:10]=[C:11]([CH3:16])[CH:12]=[C:13]([CH3:15])[N:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 7760484,6-Dimethyl-2-(4-nitrophenoxy)pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 7670374-((4,6-Dimethylpyrimidin-2-yl)oxy)anilineYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

24.5 g (0.1 mole) of 2-(4-nitro-phenoxy)-4,6-dimethyl-pyrimidine were dissolved in 150 ml of dioxane and subjected to exhaustive hydrogenation with hydrogen in the presence of Raney nickel under a pressure of 50 bar at a temperature between 20° and 50° C. The catalyst was then filtered off with suction and the filtrate was evaporated under reduced pressure. 20.4 g (95% of theory) of 2-(4-amino-phenoxy)-4,6-dimethylpyrimidine were obtained in the form of a solid substance.

Workup

  1. customat a temperature between 20° and 50° C
  2. filtrationThe catalyst was then filtered off with suction
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f1982e4efde24d49811c8caffc57f963
Source dataset
uspto-grants-1986_12
Patent number
US04627871

Linked notes

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