Dimethylformamide → 3-(4-Nitrophenyl)propanamide

To a mixture of 3-(4-nitrophenyl)propionic acid (13.45 g), N,N-dimethylformamide (0.1 mL) and tetrahydrofuran (300 mL) was added dropwise oxalyl chloride (10.5 g) at room temperature. The reaction mixture was stirred at room temperature for 1 hr. and concentrated. The obtained residue was dissolved in tetrahydrofuran (50 mL) and added dropwise to a mixture of 25% aqueous ammonia (100 mL) and tetrahydrofuran (100 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 hrs. and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 3-(4-nitrophenyl)propanamide as colorless crystals (11.80 g, yield 88%). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 177-178° C.

1. concentrationand concentrated
2. dissolutionThe obtained residue was dissolved in tetrahydrofuran (50 mL)
3. additionadded dropwise to a mixture of 25% aqueous ammonia (100 mL) and tetrahydrofuran (100 mL) at room temperature
4. stirringThe reaction mixture was stirred at room temperature for 2 hrs
5. extractionand the mixture was extracted with ethyl acetate
6. washThe organic layer was washed with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated

ORD record

ord-ea5b580fe24c42d0a1fa73ad4b83aaff

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423159B2