HCID 15057055, compound → 4-phenoxypyridin-3-amine

HRID 1032693Notes

Reaction equation

HRID 1032693 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>C(O)C.[Pd]>[O:10]([C:9]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[NH2:1])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 15057055HCID 15057055, compound

Product 1

HCID 150570594-phenoxypyridin-3-amineYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of 10% Pd/C in 5 ml of absolute ethanol was added 3-nitro-4-phenoxypyridine (7.5 g) in 245 ml of ethanol. This mixture was shaken on a Parr apparatus for two hours. The mixture was filtered and the filtrate concentrated to yield an oil (6.4 g) which was eluted with ethyl acetate on a silica gel column in HPLC. The desired fractions were concentrated to yield an oil (4.5 g). This material was distilled using a Kugelrohr apparatus to yield an oil (1.8 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-8ad0e2267f7148c082922b22703cc09f
Source dataset
uspto-grants-1990_09
Patent number
US04959377

Reaction notes

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