4-Fluoroaniline → HCID 10476762, compound

HRID 1376756Notes

Reaction equation

HRID 1376756 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9](O[Si](C)(C)C)=[C:8](O[Si](C)(C)C)[CH2:7][C:6]=1[C:21]([O:23][CH3:24])=[O:22])=[O:4].[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([F:25])=[CH:27][CH:28]=2)=[C:9]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([F:25])=[CH:27][CH:28]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 10022190HCID 10022190, compound

Product 1

HCID 10476762HCID 10476762, compound

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 2.3 ml (24 mmol) of 4-fluoroaniline in 60 ml of glacial acetic add is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 2:1 and the product fractions are concentrated by evaporation and recrystallized from ethyl acetate/hexane, yielding the title compound in the form of yellow crystals, 1H-NMR (CDCl3): δ7.40 (s, 2H), 7.10-6.80 (m, 8H), 5.70 (br s, 2H) 3.83 (s, 6H).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated off
  4. dissolutionthe dark-brown residue is dissolved in dichloromethane the solution
  5. washis washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 2:1
  9. concentrationthe product fractions are concentrated by evaporation
  10. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-15be4958b2d24cc28a884a6978cddab2
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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