4-Nitroaniline → N-(4-Nitrophenyl)pyridin-2-amine

HRID 450064Notes

Reaction equation

HRID 450064 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[K+]>CS(C)=O.C(OCC)(=O)C.O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 74754-NitroanilineHCID 79732-BromopyridineHCID 14797Potassium Hydroxide

Product 1

HCID 12695755N-(4-Nitrophenyl)pyridin-2-amineYield 9%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-nitro aniline (2 g, 14.48 mmol) and 2-bromo pyridine (3.43 g, 21.72 mmol) in DMSO (12 ml) was added powdered potassium hydroxide (3.24 g, 57.92 mmol) at room temperature and the reaction mixture was heated at 100° C. for 15 hr. The reaction mixture was diluted with ethyl acetate, and water added. The organic layer was separated, washed with brine, dried and evaporated to give crude material. Purification by column chromatography using hexane/ethyl acetate (96:4) yielded (4-nitro-phenyl)-pyridin-2-yl-amine (0.28 g, 9%).

Workup

  1. additionadded
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated
  6. customto give crude material
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-ddeb42bdee9b4d81b78cbedfac671330
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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