3-(3-Nitro-phenyl)-acrylonitrile → 3-(3-Amino-phenyl)-acrylonitrile

A solution of 3-(3-nitro-phenyl)-acrylonitrile (500 mg, 2.87 mmol) in 5% aqueous AcOH (10 ml) was heated to 80° C. Iron powder (1.44 g, 25.8 mmol) was then added and the resulting mixture was stirred for 3 h. The reaction mixture was filtered through celite and the filter cake washed with MeCN (4×50 ml). The combined MeCN layers were evaporated in vacuo and the residue was re-dissolved in EtOAc (30 ml) and HCl (30 ml). The aqueous layer was separated, basified to pH 10 with 6M NaOH, and extracted with EtOAc (3×80 ml). The combined organic layers were dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound.

1. filtrationThe reaction mixture was filtered through celite
2. washthe filter cake washed with MeCN (4×50 ml)
3. customThe combined MeCN layers were evaporated in vacuo
4. dissolutionthe residue was re-dissolved in EtOAc (30 ml)
5. customThe aqueous layer was separated
6. extractionextracted with EtOAc (3×80 ml)
7. dry with materialThe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. customthe solvent removed in vacuo

ORD-Eintrag

ord-7187499009b94848ac927764d43c9278

Quelldatensatz

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07662839B2