2-Methoxy-5-(4-nitro-phenyl)-pyridine → 4-(6-Methoxypyridin-3-yl)aniline

HRID 1711298Notes

Reaction equation

HRID 1711298 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[CH:5][N:4]=1>CCO.[Pd]>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 587548452-Methoxy-5-(4-nitro-phenyl)-pyridine

Product 1

HCID 114355844-(6-Methoxypyridin-3-yl)anilineYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-methoxy-5-(4-nitro-phenyl)-pyridine (as prepared in the previous step, 102 mg, 0.443 mmol) and 5% Pd—C (80 mg) was stirred under 1 atm H2 in 4 mL of EtOH for 4 h and then filtered through Celite and concentrated in vacuo to afford 73 mg (82%) of the title compound. Mass spectrum (ESI, m/z): Calcd. for C12H12N2O, 201.0 (M+H), found 201.3.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcfc628da3964df59ac8e62b5ea4db5a
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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