Hydrochloric Acid → 1-(2-Aminophenyl)-3-methylbutan-1-one

HRID 1359945Notes

Reaction equation

HRID 1359945 reaction equation
[C:1](#N)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[Mg].[CH2:11]([Mg]Br)[CH:12]([CH3:14])[CH3:13].Cl.[O:18]1CCCC1>C(OCC)C.O>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1](=[O:18])[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 729132-AminobenzonitrileHCID 5462224MagnesiumHCID 178418816HCID 178418816, compound

Product 1

HCID 122976091-(2-Aminophenyl)-3-methylbutan-1-oneYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

At reflux, a solution of 29.5 g (0.25 mol) of anthranilonitrile in 150 ml of tetrahydrofuran is added dropwise to a suspension comprising 18.2 g (0.75 mmol) of magnesium, 375 ml of a 2 M solution of isobutylmagnesium bromide in tetrahydrofuran and 15 ml of diethyl ether. After 5 h of heating under reflux, 100 ml of water are, at 0° C., added to the reaction mixture, and the pH is adjusted to 6 using hydrochloric acid. The organic phase is washed with water and dried over magnesium sulphate. Concentration under reduced pressure and purification on silica gel (mobile phase: petroleum ether/acetonitrile 95:5) gives 11.0 g (25% of theory) of 1-(2-aminophenyl)-3-methylbutan-1-one of logP (pH 2.3)=2.89.

Workup

  1. temperatureAt reflux
  2. temperatureAfter 5 h of heating
  3. temperatureunder reflux
  4. customare, at 0° C.
  5. additionadded to the reaction mixture
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationConcentration
  9. customunder reduced pressure and purification on silica gel (mobile phase: petroleum ether/acetonitrile 95:5)

Sources & evidence

ORD record
ord-418285991c7942cc8a83bd07fc44e18b
Source dataset
uspto-grants-2011_02
Patent number
US07879760B2

Reaction notes

Loading…