Hydrochloric Acid → (2-Aminophenyl)(cyclohexyl)methanone

HRID 476745Notes

Reaction equation

HRID 476745 reaction equation
[Mg].[I-].[CH:3]1(Br)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[NH2:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#N.Cl.[OH-:20].[Na+]>O1CCCC1.C(OCC)C>[CH:3]1([C:13]([C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[NH2:10])=[O:20])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7960Cyclohexyl bromideHCID 14798Sodium HydroxideHCID 30165Iodide Ion2×HCID 729132-AminobenzonitrileHCID 5462224Magnesium

Product 1

HCID 15634733(2-Aminophenyl)(cyclohexyl)methanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3.1 g of magnesium turnings, 10 ml of ethyl ether and several pieces of iodide were placed in a flask under a nitrogen gas, and the mixture was refluxed to fade out the color caused by iodide. 90 ml of an ethyl ether solution containing 20 g of cyclohexyl bromide was added dropwise over a 30-minute period under reflux with stirring. The temperature of the reaction solution was returned to room temperature, 40 ml of a tetrahydrofuran solution containing 4.8 g of 2-aminobenzonitrile was added dropwise over a 30-minute period, and the mixture was stirred for 30 minutes. 150 ml of an aqueous 1N hydrochloric acid solution was cautiously added, and the mixture was neutralized with a dilute aqueous sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1) and recrystallized from ethyl acetate-n-hexane to give 6.2 g of 2-cyclohexylcarbonylaniline.

Workup

  1. temperaturethe mixture was refluxed
  2. additionwas added dropwise over a 30-minute period
  3. temperatureunder reflux
  4. customwas returned to room temperature
  5. additionwas added dropwise over a 30-minute period
  6. stirringthe mixture was stirred for 30 minutes
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed, in turn, with water
  9. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1)
  12. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-79d3f309f78841a29f882f32fb76819d
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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