Aniline → (6-Fluoro-3-nitro-2-phenylaminophenyl)acetonitrile

HRID 243242Notes

Reaction equation

HRID 243242 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[CH2:12][C:13]#[N:14].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O.O>[F:11][C:4]1[C:3]([CH2:12][C:13]#[N:14])=[C:2]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 665453902-(2,6-Difluoro-3-nitrophenyl)acetonitrile

Product 1

HCID 68157927(6-Fluoro-3-nitro-2-phenylaminophenyl)acetonitrileYield 18%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of (2,6-difluoro-3-nitrophenyl)acetonitrile (4 g, 20.1 mmol) and aniline (1.83 mL, 20.1 mmol) in DMSO (20 mL) was heated at 100° C. for 16 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to yield the title compound as brown oil (959 mg, 18%). 1H NMR 400 MHz 6 (CDCl3): 8.27 (1H, dd, J=9.4, 5.9 Hz), 7.38-7.32 (2H, m), 7.17-7.12 (1H, m), 6.98-6.90 (3H, m), 3.44 (2H, d, J=1.7 Hz).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-8dfc039a63254ee4af75f2ab73bb69fd
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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