Aniline → (2-Nitropyridin-3-yl)phenylamine

HRID 242970

Reaction equation

HRID 242970 reaction equation
F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>CN(C=O)C>[N+:8]([C:3]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 27628023-Fluoro-2-nitropyridine

Product 1

HCID 20184004(2-Nitropyridin-3-yl)phenylamineYield 154.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-fluoro-2-nitropyridine (1.07 g, 6.75 mmol), aniline (1.8 mL, 20.2 mmol) and Et3N (2.8 mL, 20.2 mmol) in DMF (10 mL) was stirred at 100° C. for 16 h under a nitrogen atmosphere. After cooling to RT, the volatiles were removed under reduced pressure. The resulting residue was partitioned between DCM and water. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM) to afford the title compound as a red oil (2.24 g, quantitative). LCMS (Method C): RT 3.03 min [M+H]+ 216.2.

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed under reduced pressure
  3. customThe resulting residue was partitioned between DCM and water
  4. extractionThe aqueous phase was further extracted with DCM (×3)
  5. dry with materialthe combined organic fractions dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% MeOH in DCM)

Sources & evidence

ORD record
ord-8f761dc54c3a4619aa346344671b6aeb
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Linked notes

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