Aniline → (3-Fluoro-2-methoxy-6-nitrophenyl)phenylamine

HRID 243237Notes

Reaction equation

HRID 243237 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[C:3]=1[O:12][CH3:13].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CS(C)=O.O>[F:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 681577701,3-Difluoro-2-methoxy-4-nitrobenzene

Product 1

HCID 68157646(3-Fluoro-2-methoxy-6-nitrophenyl)phenylamine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1,3-difluoro-2-methoxy-4-nitrobenzene (1 g, 5.29 mmol) and aniline (0.53 mL, 5.82 mmol) in DMSO (10 mL) was heated at 100° C. for 4 h. The reaction mixture was diluted with water and the product extracted with EtOAc (3×15 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 0-50% Et2O in cyclohexane) to yield the title compound as an off white solid (1.05 g, 76%). 1H NMR 400 MHz δ (CDCl3): 8.82 (1H, br s), 7.96 (1H, dd, J=9.5, 5.3 Hz), 7.32-7.26 (2H, m), 7.12-7.07 (1H, m), 7.02-6.98 (2H, m), 6.74 (1H, t, J=9.5 Hz), 3.53 (3H, d, J=1.1 Hz).

Workup

  1. extractionthe product extracted with EtOAc (3×15 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 0-50% Et2O in cyclohexane)

Sources & evidence

ORD record
ord-65ed39809a984c96bc4ae57d94fc264c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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