Acetic Acid → N,N-Dibutyl-4-nitroaniline

Participants

Reaction Steps

To a solution of 4-nitroaniline (1.4 g, 10 mmol) in 1,2-dichloroethane (10 ml) at 0° C. was added butyraldehyde (1.8 g, 25 mmol). The reaction mixture was stirred for 0.5 hour, then sodium triacetoxyborohydride (5.3 g, 25 mmol) and acetic acid (1 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. Solvent were removed under reduced pressure and the residue purified on column of silica gel to provide the titled 4-nitro-N,N-dibutylaniline (1.1 g, 44%) as a yellow solid. 1HNNMR (CDCl3, 300 MHz), δ ppm 8.10 and 6.58 (d, J=9 Hz, 4H, Ar—H), 3.36 (t, J=9.0 Hz, 4H, 2 NCH2), 1.6 (m, 4H, 2CH2), 1.48 (m, 4H, 2CH2), 0.98 (t, 6H, 2CH3), MS (ESI) (M+1)+ 251.

Provenance & Evidence