Sodium Dithionite → 2,3-Diamino-5,6-dichlorotoluene

Participants

Reaction Steps

A solution of sodium dithionite (94 g, 0.54 mol) in water (1 L) was added to a stirred mixture of 3-amino-5,6-dichloro-2-nitrotoluene (39.7 g, 0.18 mol) and potassium bicarbonate (94 g, 0.94 mmol) in methanol (1 L) at room temperature. After 30 minutes, the mixture was concentrated under reduced pressure and the resulting suspension extracted with ethyl acetate (total of 700 mL). The extracts were dried (MgSO4) and concentrated under reduced pressure to give 2,3-diamino-5,6-dichlorotoluene (26.1 g, 38% over 2 steps) as a brown solid. 1H NMR (300 MHz, CDCl3) 2.28 (3H, s), 3.36 (2H, br s), 3.42 (2H, br s), 6.72 (1H, s).

Provenance & Evidence