3-Methyl-5-nitro-2-phenylpyridine → 5-Methyl-6-phenylpyridin-3-amine

HRID 41979Notes

Reaction equation

HRID 41979 reaction equation
[CH3:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 463150573-Methyl-5-nitro-2-phenylpyridine

Product 1

HCID 135028615-Methyl-6-phenylpyridin-3-amineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-methyl-5-nitro-2-phenylpyridine (4.43 mmol, 0.95 g) and Pd/C 10% (0.1 g) in ethanol (40 ml) was stirred for 16 hours under hydrogen atmosphere. The catalyst was filtered off and the solid thoughtfully washed with warm ethanol. The filtrate was evaporated and the crude was purified by chromatography over SiO2 eluting with DCM/methanol mixtures and affording 0.65 g (yield 80%) of the expected product.

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe solid thoughtfully washed with warm ethanol
  3. customThe filtrate was evaporated
  4. customthe crude was purified by chromatography over SiO2 eluting with DCM/methanol mixtures

Sources & evidence

ORD record
ord-6f18cdd6490146a180833350eb45a046
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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