Reaktion #7793

Reaktionsgleichung

[4-(1,3-benzoxazol-2-yl)-2-nitrophenyl]acetonitrile

→

[2-amino-4-(1,3-benzoxazol-2-yl)phenyl]acetonitrile

Lösungsmittel

EtOH EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   Filtrationwas filtered through Celite
3. 3
   Sonstigethe filtrate was evaporated to dryness
4. 4
   SonstigeThe yellow solid obtained
5. 5
   Sonstigewas purified by flash chromatography on silica gel eluting with MeOH:CH2Cl2 (1:19)

Vorschrift

A suspension of [4-(1,3-benzoxazol-2-yl)-2-nitrophenyl]acetonitrile (100 mg, 0.36 mmol) and Pd/C (20 mg) in EtOH/EtOAc (5:1, 60 mL) was hydrogenated (35 psi) over 2d. The resulting reaction mixture was filtered through Celite and the filtrate was evaporated to dryness. The yellow solid obtained was purified by flash chromatography on silica gel eluting with MeOH:CH2Cl2 (1:19) to afford [2-amino-4-(1,3-benzoxazol-2-yl)phenyl]acetonitrile as an orange solid (M.p. 198–199° C.). 1H NMR (CDCl3, 300 MHz) δ 7.77 (m, 1H), 7.71–7.66 (m, 2H), 7.58 (m, 1H), 7.40–7.34 (m, 3H), 3.88 (s, 2H), 3.66 (s, 2H). MS (ESI) 250 (M+H)+.

Quelle