Hydrochloric Acid → 1-(2-aminophenyl)-2-methylpropan-1-one

HRID 1596335Notes

Reaction equation

HRID 1596335 reaction equation
[Mg].[CH:2](Br)([CH3:4])[CH3:3].[NH2:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#N.Cl.CC[O:18]CC>O1CCCC1>[CH:2]([C:9]([C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=1[NH2:6])=[O:18])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 63582-BromopropaneHCID 729132-AminobenzonitrileHCID 5462224Magnesium

Product 1

HCID 122976071-(2-aminophenyl)-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of magnesium turnings (7.53 g) in dry ether (100 ml) was added dropwise a solution of isopropyl bromide (36.87 g) in dry ether (50 ml) at reflux temperature for 1 hour. The mixture was heated at the same temperature for 1 hour and then allowed to cool to 5˜10° C. in an ice bath. To the mixture was added dropwise a solution of 2-aminobenzonitrile (11.81 g) in dry tetrahydrofuran (100 ml) at the same temperature for 1 hour. The mixture was stirred additionally 1 hour and then heated under reflux for 3 hours. The reaction mixture was allowed to cool to 5˜10° C. in an ice bath. A 3N aqueous hydrochloric acid was added dropwise to the mixture for 1 hour and then heated under reflux for 3 hours. The resultant mixture was concentrated in vacuo to remove the organic solvent. The residue was extracted with chloroform (2×300 ml). The extracts were combined and washed with a brine (2×100 ml). Dryness over magnesium sulfate and evaporation gave a crude product. The product was purified by column chromatography on silica gel with chloroform. The fractions containing the desired product were combined and evaporated in vacuo to afford a pure 2-isopropylcarbonylaniline (15.35 g) as a colorless oil.

Workup

  1. temperatureat reflux temperature for 1 hour
  2. temperatureThe mixture was heated at the same temperature for 1 hour
  3. temperatureto cool to 5˜10° C. in an ice bath
  4. temperatureheated
  5. temperatureunder reflux for 3 hours
  6. temperatureto cool to 5˜10° C. in an ice bath
  7. temperatureheated
  8. temperatureunder reflux for 3 hours
  9. concentrationThe resultant mixture was concentrated in vacuo
  10. customto remove the organic solvent
  11. extractionThe residue was extracted with chloroform (2×300 ml)
  12. washwashed with a brine (2×100 ml)
  13. customDryness over magnesium sulfate and evaporation
  14. customgave a crude product
  15. customThe product was purified by column chromatography on silica gel with chloroform
  16. additionThe fractions containing the desired product
  17. customevaporated in vacuo

Sources & evidence

ORD record
ord-1b99ca2116b945678e70a61c9c4e25f7
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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