Hydrazine hydrate (1:1) → 5-Methoxy-o-toluidine

Participants

Reaction Steps

To a solution of 4-methoxy-1-methyl-2-nitrobenzene (18.0 g, 108 mmol) in 160 mL of DME was added Pd/C (10%, 0.9 g) under nitrogen. Then hydrazine hydrate (16.17 g, 323 mmol) was added dropwise. The mixture was heated and stirred under reflux for 4 h. Then another 3 mL of hydrazine hydrate was added and stirred under reflux for 2d. Then the reaction mixture was cooled to RT, filtered through celite and evaporated to dryness to give 5-methoxy-2-methylaniline as yellow oil that solidified upon drying under vacuum to give 14.8 g (100%). 1H NMR (300 MHz, CDCl3): δ 6.94 (d, J=7.53 Hz, 1H), 6.28 (d, J=7.53 Hz, 1H), 6.26 (s, 1H), 3.78 (s, 3H), 3.5 (br, 1H), 2.10 (s, 3H), 1.6 (br, 1H).

Provenance & Evidence