Aniline → Nitrobenzene

HRID 749631Notes

Reaction equation

HRID 749631 reaction equation
NC1C=CC=CC=1.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16]>C(N(C(C)C)CC)(C)C>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:9]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 6115AnilineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 7416NitrobenzeneYield 402.9%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
120 °C

Procedure

0.46 mL (5.0 mmole) of aniline was added to a 10 mL diisopropylethylamine solution of 437 mg (1.0 mmole) of fluoronitrobenzene compound (1B-8) and the mixture was stirred for 16 hours at 120° C. The solvent was removed under reduced pressure, 1N hydrochloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure, yielding 496 mg (97 percent) of nitrobenzene compound (1B-9).

Workup

  1. customThe solvent was removed under reduced pressure, 1N hydrochloride
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-49cb82d0c40d4d83bdef4916396a07c6
Source dataset
uspto-grants-2008_07
Patent number
US07402696B2

Reaction notes

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