3-(4-bromophenyl)propanamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-(4-bromophenyl)propanamide (1.59 g) in tetrahydrofuran (24 ml) was added lithium aluminum hydride (370 mg) and the mixture was refluxed for 1.5 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into 1N aqueous sodium hydroxide solution (100 ml). The mixture was extracted with ethyl acetate and the organic layer was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave 3-(4-bromophenyl)-1-propanamine (1.55 g) as a yellow oil. the mixture was refluxed for 1.5 hours under nitrogen atmosphere The mixture was extracted with ethyl acetate the organic layer was washed with water and brine dried over magnesium sulfate Filtration followed by evaporation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-(4-bromophenyl)propanoic acid (15.0 g) in thionyl chloride (24.5 g) was added catalytic amount of N,N-dimethylformamide (one drop) and refluxed for 1.5 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured slowly into 28% aqueous ammonium hydroxide solution (150 ml) at 0° C. The mixture was extracted with ethyl acetate, washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave 3-(4-bromophenyl)propanamide (13.7 g) as a white solid. refluxed for 1.5 hours under nitrogen atmosphere The mixture was extracted with ethyl acetate washed with water and brine dried over magnesium sulfate Filtration followed by evaporation under reduced pressure