3-(4-Nitrophenyl)-4-phenylpyridine → 4-(4-Phenylpyridin-3-yl)aniline

HRID 1405069Notes

Reaction equation

HRID 1405069 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[C:16]1([C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 232466833-(4-Nitrophenyl)-4-phenylpyridine

Product 1

HCID 667140694-(4-Phenylpyridin-3-yl)anilineYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Intermediate 13B in MeOH (3 mL) was added Pd/C (33.2 mg, 0.031 mmol). The resulting mixture was stirred under H2 atmosphere for 2 hours and then filtered through a pad of CELITE®/silica. The filtrate was concentrated to yield the Intermediate 13 (100 mg, 0.406 mmol, 78% yield). MS (ES): m/z=247.0 [M+H]+. Intermediate 13 was used in the synthesis of the compounds of Examples 8 and 9.

Workup

  1. filtrationfiltered through a pad of CELITE®/silica
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d690477bbc6143f79bc7523c7373e9e5
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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