Aniline → HCID 22397864, compound

HRID 460507Notes

Reaction equation

HRID 460507 reaction equation
F[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)(=O)C>[C:13]1([NH:12][C:2]2[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 22397864HCID 22397864, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

14 g of 3-fluoro-4-nitrophenol and 24 ml of aniline were mixed and stirred for 3 hours at 140° C. After cooling, it was dissolved in ethyl acetate and extracted six times with 2N aqueous hydrochloric acid. The organic phase was washed with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was crystallized from diisopropyl ether. 20.8 g was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted six times with 2N aqueous hydrochloric acid
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customthe residue was crystallized from diisopropyl ether
  7. custom20.8 g was obtained

Sources & evidence

ORD record
ord-79f56338b5814f1b8a0281312f0f75e8
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Reaction notes

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