3-Nitro-2-phenoxypyridine → N-Hydroxy-2-phenoxypyridin-3-amine

HRID 1601139Notes

Reaction equation

HRID 1601139 reaction equation
[N+:1]([C:4]1[C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=[O:2].[H][H]>[Pt].CN1CCOCC1>[O:10]([C:5]1[C:4]([NH:1][OH:2])=[CH:9][CH:8]=[CH:7][N:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 9018963-Nitro-2-phenoxypyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 21831171N-Hydroxy-2-phenoxypyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 79724-MethylmorpholineSolvent

Procedure

A mixture of 9.2 g (43 mmol) of 3-nitro-2-phenoxypyridine (Example 1.a) and 100 ml of N-methylmorpholine was hydrogenated at room temperature (approximately 25° C.) and an H2 pressure of approximately 1.1 bar in the presence of 1 g of 5% platinum/charcoal (51% water; manufactured by Degussa). The hydrogen uptake ceased after approximately 2 hours. The catalyst was removed by filtration through active charcoal. The resulting solution was freed from solvent under reduced pressure ("high vacuum"). This gave 7.8 g (90%) of the title compound as a white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. custom(approximately 25° C.)
  3. customThe catalyst was removed by filtration through active charcoal

Sources & evidence

ORD record
ord-e70011adb901483ea4f138c98a1436b1
Source dataset
uspto-grants-1999_11
Patent number
US05977146

Reaction notes

Loading…