2-Nitroaniline → N-(2-Nitrophenyl)pyridin-2-amine

HRID 2262428Notes

Reaction equation

HRID 2262428 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Cu](I)I>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 69462-NitroanilineHCID 79732-BromopyridineHCID 11430Potassium Carbonate

Product 1

HCID 59785875N-(2-Nitrophenyl)pyridin-2-amineYield 27%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

Under the atmosphere of nitrogen gas, 15.0 g (109 mmol) of 2-nitroaniline, 17.2 g (109 mmol) of 2-bromopyridine, 2.06 g (10.9 mmol) of copper iodide and 30 g (218 mmol) of potassium carbonate were stirred with heating at the temperature of 160° C. for 9 hours. The reacted solution was cooled down to room temperature, diluted with ethyl acetate and filtered. After concentrating the filtrate, it was refined with silicagel column chromatography, and 6.30 g of 2-nitro-N-pyridyl aniline was obtained (yield: 27%).

Workup

  1. temperatureThe reacted solution was cooled down to room temperature
  2. filtrationfiltered
  3. concentrationAfter concentrating the filtrate, it

Sources & evidence

ORD record
ord-d5eb9388e0a74d689de12b503f00e980
Source dataset
uspto-grants-2010_12
Patent number
US07851071B2

Reaction notes

Loading…