Aniline → HCID 10633103, compound

HRID 242807Notes

Reaction equation

HRID 242807 reaction equation
F[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]1([NH2:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-

Product 1

HCID 10633103HCID 10633103, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-fluoro-4-methyl-1-nitrobenzene (1.0 g, 6.45 mmol) in DMSO (3 mL) was purged with a stream of nitrogen prior to addition of phenylamine (1.18 mL, 12.9 mmol) and then stirred in a sealed tube at 100° C. for 20 h. After cooling to RT, the reaction mixture was partitioned between EtOAc (125 mL) and water (150 mL). The organic layer was then washed with water (150 mL×3), followed by brine, then dried (Na2SO4) and concentrated in vacuo affording (5-Methyl-2-nitrophenyl)phenylamine as a red solid (1.5 g, quantitative). 1H NMR (DMSO, 400 MHz): δ 9.40 (1H, s), 8.03 (1H, d, J=8.70 Hz), 7.45-7.39 (2H, m), 7.35-7.30 (2H, m), 7.21 (1H, t, J=7.33 Hz), 6.98 (1H, s), 6.72-6.68 (1H, m), 2.24 (3H, s).

Workup

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was partitioned between EtOAc (125 mL) and water (150 mL)
  3. washThe organic layer was then washed with water (150 mL×3)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c4ca9e687fc45d0868741bcdf9deb87
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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