Hydrochloric Acid → 2-(4-Isobutylphenyl)propionamide hydrochloride
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:14])[C:12]#[N:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[ClH:15].C([O:18]CC)C.CO>>[ClH:15].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:14])[C:12]([NH2:13])=[O:18])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]Participants
Conditions
- Temperature
- 2.5 °C
Procedure
A solution of 2-(4-isobutylphenyl)propionitrile (0.2 g; 1.07 mmol) in a (1:1) diethyl ether/methyl alcohol mixture (20 mL) is cooled at T=0-5° C. and gaseous HCl is bubbled into the solution for 1 h. Then the temperature is left to arise to r.t. and the mixture stirred overnight. After solvent evaporation under reduced pressure, the crude is dissolved in methyl alcohol (10 mL) and cooled at T=0-5° C. Ammonia is bubbled into for 1 h and the resulting mixture is left stirring overnight at r.t. After solvent evaporation under reduced pressure, the crude is suspended in diethyl ether (15 mL) and left stirring at r.t. for 2 h. The 2-(4-isobutylphenyl)propionamide hydrochloride (I) is isolated by filtration in vacuo as white solid (0.193 g; 0.80 mmol). Yield 75%. 1H-NMR (DMSO-d6): δ 8.80-8.50 (bs, NH3+Cl−); 7.40 (d, 2H, J=7 Hz); 7.15 (d, 2H, J=7 Hz); 3.98 (q, 1H, J=8 Hz); 2.42 (d, 2H, J=8 Hz); 1.90 (m, 1H); 1.57 (d, 3H, J=8 Hz); 0.88 (d, 6H, J=8 Hz).
Workup
- customis bubbled into the solution for 1 h
- waitThen the temperature is left
- customto arise to r.t.
- customAfter solvent evaporation under reduced pressure
- dissolutionthe crude is dissolved in methyl alcohol (10 mL)
- customAmmonia is bubbled into for 1 h
- waitthe resulting mixture is left
- stirringstirring overnight at r.t
- customAfter solvent evaporation under reduced pressure
- waitleft
- stirringstirring at r.t. for 2 h
Sources & evidence
- ORD record
- ord-6e3f75c614bd4ad4b427931e90a184f6
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674806B2
Reaction notes
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