Potassium Acetate → 5-Phenylpyridin-3-amine

HRID 41986Notes

Reaction equation

HRID 41986 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([N+:14]([O-])=O)=[CH:4][N:3]=1.CC([O-])=O.[K+]>C(O)C.[Pd]>[C:8]1([C:7]2[CH:6]=[C:5]([NH2:14])[CH:4]=[N:3][CH:2]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 463146982-Chloro-5-nitro-3-phenylpyridine

Product 1

HCID 27629015-Phenylpyridin-3-amineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-5-nitro-3-phenylpyridine (0.43 mmol, 0.1 g), KOAc (0.43 mmol, 0.042 g) and Pd/C 10% (0.03 g) in ethanol (4 ml) was stirred for 24 hours under hydrogen atmosphere. The catalyst was filtered off and the solid thoughtfully washed with warm ethanol. The solid residue was purified by chromatography over SiO2 eluting with dichloromethane/methanol mixtures affording 5-phenylpyridin-3-amine (0.05 g, yield 69%) of the expected product.

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe solid thoughtfully washed with warm ethanol
  3. customThe solid residue was purified by chromatography over SiO2 eluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-2d7ac8cb0c5048eeba8ab1e599705f42
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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