3,5-Dinitrobenzyl alcohol → (3-Amino-5-nitrophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dinitrobenzyl alcohol (129.1 g, 0.65 mol; from step (i) above) in MeOH (1500 mL) at reflux was added ammonium sulfide (450 mL, 442.9 g of 20 wt % in H2O, 1.30 mol) over 45 min. The resulting heterogeneous mixture was refluxed for 2 h and stirred at 25° C. for 18 h. The solution was filtered through a pad of Celite, the filtrate was acidified with 2N HCl and the MeOH distilled off in vacuo. The remaining acidic aqueous solution was washed with Et2O (3×) and basified with 6N NaOH. The basic aqueous solution was extracted with Et2O (4×). The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 95.8 g (88%) of the sub-title compound as an orange solid which was used without further purification.

Provenance & Evidence