2-Aminofluorene → 3-(2-Fluorenylamino)-4-nitrophenol

HRID 2054637Notes

Reaction equation

HRID 2054637 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:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C:15]=2[CH:14]=1>C(OCC)(=O)C>[CH:14]1[C:15]2[CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]=2[CH:24]=[CH:25][C:13]=1[NH:12][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 15392-AminofluoreneHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 219381213-(2-Fluorenylamino)-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

2.17 g of 3-fluoro-4-nitrophenol and 5 g of 2-aminofluorene were mixed and stirred for 9 hours at 140° C. The raw mixture was taken up in ethyl acetate and water and washed with 1N aqueous hydrochloric acid. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed three times with 2N aqueous hydrochloric acid and once with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was chromatographed on silica gel.

Workup

  1. washwater and washed with 1N aqueous hydrochloric acid
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic phases were washed three times with 2N aqueous hydrochloric acid
  4. dry with materialonce with saturated sodium chloride solution, dried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-af90f54c316f41c4a9be0edb2f33ebc8
Source dataset
uspto-grants-2008_02
Patent number
US07329679B2

Reaction notes

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