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0 °C

Concentrated HCl (1.54 mL) was added to a suspension of (Z)-2-nitro-6-(prop-1-enyl)benzonitrile (Example 3c) (0.35 g, 1.86 mmol) in MeOH (30 mL) and 1,4-dioxane (15 mL) at room temperature, followed by portion wise addition of iron powder (0.73 g, 13.0 mmol). The obtained mixture was heated at refluxed for 2.5 h, cooled to 0° C. and the pH was adjusted to pH˜10 with aqueous 50% solution of NaOH. The mixture was extracted with EtOAc (3×50 mL), the combined extract was dried with MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with gradient 0% to 100% DCM in hexanes, to give 0.24 g (80%) of (Z)-2-amino-6-(prop-1-enyl)benzonitrile as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 7.24-7.30 (m, 1H), 6.68 (d, J=8.4 Hz, 1H), 6.55 (d, J=7.2 Hz, 1H), 6.42-6.48 (m, 1H), 5.98 (broad s, 2H), 5.89-5.97 (m, 1H), 1.74-1.78 (m, 3H). MS 159 (MH+).

1. temperatureThe obtained mixture was heated
2. temperatureat refluxed for 2.5 h
3. extractionThe mixture was extracted with EtOAc (3×50 mL)
4. extractionthe combined extract
5. dry with materialwas dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by chromatography on silica gel eluting with gradient 0% to 100% DCM in hexanes