3-Nitrophenylacetonitrile → (3-Amino-phenyl)-acetonitrile

A solution of 3-nitrophenyl acetonitrile (500 mg, 3.1 mmol) in 5% AcOH (10 ml) was heated to 80° C. Iron powder (1.5 g, 27 mmol) was then added and the resulting mixture stirred for 2 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) followed by 2M 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 record

ord-51f4b46f11d84c9fb35ba3fed6c3a6a5

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326732B2