3-Nitro-N-(pyridin-2-yl)pyridin-2-amine → 2-(2-Pyridylamino)-3-amino-pyridine

HRID 243051Notes

Reaction equation

HRID 243051 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].CCOC(C)=O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 1

HCID 133823723-Nitro-N-(pyridin-2-yl)pyridin-2-amine

Product 1

HCID 133823752-(2-Pyridylamino)-3-amino-pyridineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of (3-nitro-pyridin-2-yl)-pyridin-2-yl-amine (0.84 g, 3.89 mmol) and 10% palladium on carbon (0.30 g) in EtOAc (20 mL) was stirred under an atmosphere of hydrogen at atmospheric pressure and 20° C. for 16 h. The catalyst was removed by filtration and the filtrate concentrated in vacuo to give the title compound as a green solid (0.63 g, 88%). LCMS (method H): Rt 1.87 min, [M+H]+ 187.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-bcc87e67b36a4042aaf1fab5ae2e4191
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…