Ethyl Acetate → 1-(2-aminophenyl)-2-methylpropan-1-one

HRID 2293842Notes

Reaction equation

HRID 2293842 reaction equation
[C:1](#N)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH:10]([Mg]Cl)([CH3:12])[CH3:11].CC[O:17]C(C)=O>CCOCC.CCCCCC>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1](=[O:17])[CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 729132-AminobenzonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 122976071-(2-aminophenyl)-2-methylpropan-1-oneYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of anthranilonitrile (8.507 gm, 72 mmol) in dry Et2O (20 ml) was added to i-propylmagnesium chloride (2.0M in Et2O, 100 ml, 200 mmol) in dry Et2O (30 ml) at 0° C. over a 15 minute period. After the addition was complete, the mixture was warmed to room temperature and stirred for 4.5 hours. The solution was cooled to 0° C., quenched with 10% HCl (150 ml), then stirred for 25 minutes. The aqueous layer was made basic with solid NaOH (25 gm) and then extracted with Et2O (3×). The combined Et2O extracts were washed with brine, then dried (Na2SO4), filtered and stripped to give a yellow oil. Flash Chromatography of the oil (Merck SiO2, 15% EtOAc in hexane) afforded 1-(2-aminophenyl)-2-methyl-1-propanone (10.916 gm, 93%) as a golden yellow oil.

Workup

  1. additionAfter the addition
  2. temperatureThe solution was cooled to 0° C.
  3. customquenched with 10% HCl (150 ml)
  4. stirringstirred for 25 minutes
  5. extractionextracted with Et2O (3×)
  6. washThe combined Et2O extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customto give a yellow oil

Sources & evidence

ORD record
ord-89cfa566c25a447aa99e17042d6eefd1
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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