2-Nitro-6-(pyridin-2-yl)aniline → 3-(Pyridin-2-yl)benzene-1,2-diamine

HRID 589472Notes

Reaction equation

HRID 589472 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:5]=1[NH2:6])([O-])=O>CCOC(C)=O.[Pd]>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([NH2:1])[C:5]=1[NH2:6]

Participants

4

Reactant 1

HCID 130010352-Nitro-6-(pyridin-2-yl)aniline

Product 1

HCID 224661493-(Pyridin-2-yl)benzene-1,2-diamineYield 103,000%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-nitro-6-(pyridin-2-yl)aniline (XCIX) (2.4 g, 0.01 mmol, 1 eq) in EtOAc (350 mL) was added Pd/C (1 g) and the mixture was stirred at room temperature overnight, filtered and then concentrated in vacuo, to give 3-(pyridin-2-yl)benzene-1,2-diamine (1.9 g, 10.3 mmol, 89% yield) as a yellow oil. ESIMS found for C11H11N3 m/z 186 (M+H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5bce5dd692c493f95ca5ff708bbe7c7
Source dataset
uspto-grants-2016_01
Patent number
US09233104B2

Reaction notes

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