Short-RInChIKey=SA-FUHFF-UHFFFADPSC-FXWFZIRWWN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

The starting material 2-nitrobenzaldehyde (5.00 g, 33.1 mmol, 1.00 equiv) was dissolved in 22 mL of a 9:1 mixture of EtOH/H2O, followed by iron (9.24 g, 165 mmol, 5.00 equiv) and hydrochloric acid (121 mg, 33.1 mL, 3.31 mmol, 0.100M, 0.100 equiv). The orange reaction mixture was stirred at 80 °C for 3 hours. After complete conversion of the starting material according to TLC, the red solution was cooled to 25 °C and filtered through a silica plug. Then water was added and the aqueous phase was extracted 3 times with DCM. The combined organic phases were dried over Na2SO4, filtered and the solvent was removed under reduced pressure.