2-(3-Methoxyphenyl)-5-nitro-3-phenylpyridine → 6-(3-Methoxyphenyl)-5-phenylpyridin-3-amine

HRID 41997Notes

Reaction equation

HRID 41997 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][C:12]([N+:21]([O-])=O)=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][C:12]([NH2:21])=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 673943592-(3-Methoxyphenyl)-5-nitro-3-phenylpyridine

Product 1

HCID 584158776-(3-Methoxyphenyl)-5-phenylpyridin-3-amineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(3-methoxyphenyl)-5-nitro-3-phenylpyridine (0.84 mmol, 0.257 g) and Pd/C 10% (0.08 mmol, 0.009 g) in ethanol (5 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 0.160 g (yield 69%) 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-b6ed7be95b84411ca165bbe6e28bda04
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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