Water → N-Heptyl-4-fluoro-3-methylaniline

HRID 902228Notes

Reaction equation

HRID 902228 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].CS(O[CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])(=O)=O.C([O-])(O)=O.[Na+].O>C(#N)C>[CH2:18]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([CH3:9])[CH:4]=1)[CH2:17][CH2:16][CH2:15][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 679814-Fluoro-m-toluidineHCID 516892Sodium BicarbonateHCID 121363934-Methanesulfonyloxyheptane

Product 1

HCID 22322478N-Heptyl-4-fluoro-3-methylanilineYield 349.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4.10 g (3.28 mmol) of 4-fluoro-3-methylaniline in 30 mL of acetonitrile was added 7.64 g (3.93 mmol) of 4-methanesulfonyloxyheptane, and 3.4 g (4.1 mmol) of NaHCO3(s). The mixture was stirred at reflux for 24 hours, then poured into 150 mL of H2O and extracted with diethyl ether (2×30 mL). The combined ether layers were back extracted with brine (1×30 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via silica gel chromatography, eluting with 97.5:2.5 hexanes:ethyl acetate, to give 2.56 g (35%) of a pale yellow oil.

Workup

  1. temperatureat reflux for 24 hours
  2. extractionextracted with diethyl ether (2×30 mL)
  3. extractionThe combined ether layers were back extracted with brine (1×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThis was purified via silica gel chromatography
  8. washeluting with 97.5:2.5 hexanes

Sources & evidence

ORD record
ord-09bab8930d9e497f95da776de3495e26
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Reaction notes

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