3-Nitrobenzaldehyde → HCID 178526625, compound

Participants

Reaction Steps

A mixture of 3-nitrobenzaldehyde (1.51 g) and 5-aminotetrazole monohydrate (1.03 g)in absolute ethanol (30 ml) and glacial acetic acid (0.57 ml) was stirred at room temperature for 40 minutes and then refluxed under nitrogen for 5 hours 30 minutes. Solvents were removed under high vacuum and the remaining solid was suspended in absolute ethanol (50 ml) and treated at room temperature with solid sodium borohydride (1.2 g) over 20 minutes. After a further 15 hours of stirring, the solvent was removed under vacuum and the residue was dissolved in water (100 ml) and extracted with diethyl ether (2×30 ml). The basic aqueous phase was acidified to pH 2 with 2N hydrochloric acid and the precipitated solid was collected by filtration, washed with water, diethyl ether, and finally recrystallized from absolute ethanol to give the title compound (420 mg) as white needles; mp 208°-210° C.; δH (250 MHz, DMSO-d6) 8.21 (1H, br s, Ar--H), 8.12 (1H, br d, J=9 Hz, Ar--H), 7.80 (1H, d, J=8 Hz, Ar--H), 7.70 (1H, br t, J=6.3 Hz, --NH--), 7.64 (1H, t, J=8 Hz, Ar--H), 4.53 (2H, d, J=6.3 Hz, --CH2 --); m/z (CI) 220 (M-).

Provenance & Evidence