Hydrochloric Acid → 1-(2-Amino-3-methylphenyl)ethan-1-one

HRID 1596357Notes

Reaction equation

HRID 1596357 reaction equation
NC1[C:3](C)=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:9](#[N:11])[CH3:10].B(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[C:21](OCC)(=[O:23])[CH3:22]>C1(C)C=CC=CC=1>[C:21]([C:10]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:3])[C:9]=1[NH2:11])(=[O:23])[CH3:22]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 7242O-ToluidineHCID 8857Ethyl AcetateHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1796281-(2-Amino-3-methylphenyl)ethan-1-oneYield 39.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 2-toluidine (32.8 g, 0.30 ml) and acetonitrile (6.22 g, 0.15 mol) in dry toluene (200 ml) was added 1N-solution of boron trichloride in toluene (150 ml) dropwise under stirring and cooling in an ice-bath for 2 hours. After the addition was completed, the mixture was stirred for 1 hour at ambient temperature and cooled again. To the cooled mixture was added aluminum chloride (20.0 g, 0.15 mol) portionwise. The resultant mixture was stirred at ambient temperature for 1 hour and refluxed for 5 hours. After cooling the reaction mixture in an ice-bath, 2N-HCl (200 ml) was added. The mixture was then refluxed for 2.5 hours. After cooling the mixture, ethyl acetate was added. The separated organic layer was washed with water twice and dried over magnesium sulfate. Removal of the solvent in vacuo Save crystals, which was washed with n-hexane with stirring and collected by filtration to give 2-acetyl-6-methylaniline as a yellow crystal (8.91 g, 39.8%).

Workup

  1. temperaturecooling in an ice-bath for 2 hours
  2. additionAfter the addition
  3. stirringthe mixture was stirred for 1 hour at ambient temperature
  4. temperaturecooled again
  5. temperaturerefluxed for 5 hours
  6. temperatureAfter cooling the reaction mixture in an ice-bath
  7. temperatureThe mixture was then refluxed for 2.5 hours
  8. additionwas added
  9. washThe separated organic layer was washed with water twice
  10. dry with materialdried over magnesium sulfate
  11. customRemoval of the solvent in vacuo Save crystals, which
  12. washwas washed with n-hexane
  13. stirringwith stirring
  14. filtrationcollected by filtration

Sources & evidence

ORD record
ord-89619edf719d4b578d332ec2ca51faa6
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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