2-Nitro-6-(pyridin-4-yl)aniline → 3-(Pyridin-4-yl)benzene-1,2-diamine

HRID 589468Notes

Reaction equation

HRID 589468 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:5]=1[NH2:6])([O-])=O>CCOC(C)=O.[Pd]>[N:14]1[CH:13]=[CH:12][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:4]([NH2:1])[C:5]=2[NH2:6])=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 867010682-Nitro-6-(pyridin-4-yl)aniline

Product 1

HCID 867010693-(Pyridin-4-yl)benzene-1,2-diamineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-nitro-6-(pyridin-4-yl)aniline (XCIV) (3 g, 14 mmol, 1 eq) in EtOAc (350 mL) was added Pd/C (0.3 g) and the mixture was stirred at room temperature under 1 atm of H2 atmosphere overnight, the mixture was filtered and concentrated in vacuo to give the product 3-(pyridin-4-yl)benzene-1,2-diamine (XCV) (2.4 g, 13.0 mmol, 93% yield) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ ppm 4.35 (s, 2H), 4.75 (s, 2H), 6.45 (dd, J=7.6 Hz, J=1 Hz, 1H), 6.58 (t, J=7.6 Hz, 1H), 6.67 (d, J=6.8 Hz, 1H), 7.47 (d, J=6 Hz, 2H), 8.65 (d, J=6 Hz, 2H); ESIMS found for C11H11N3 m/z 186 (M+H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6405df512f364ec2a90945a607f767e3
Source dataset
uspto-grants-2016_01
Patent number
US09233104B2

Reaction notes

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