Aniline → HCID 10609383, compound

HRID 242811Notes

Reaction equation

HRID 242811 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[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:5]1[CH:6]=[CH:7][C:2]([NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 1362874-Fluoro-3-nitrotoluene

Product 1

HCID 10609383HCID 10609383, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-fluoro-4-methyl-2-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 (200 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 and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% DCM in cyclohexane) affording (4-Methyl-2-nitrophenyl)phenylamine as a red oil (1.41 g, 96%). 1H NMR (DMSO, 400 MHz): δ 9.21 (1H, s), 7.94-7.91 (1H, m), 7.43-7.26 (5H, m), 7.19-7.12 (2H, m), 2.27 (3H, s).

Workup

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was partitioned between EtOAc (200 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
  6. customthe resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% DCM in cyclohexane)

Sources & evidence

ORD record
ord-01e7caa110934fc9a8bdc2769292d7ce
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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