2,4,6-Trinitrotoluene → 4-Hydroxylamino-2,6-dinitrotoluene

Participants

Reaction Steps

To a stirred solution of TNT (1.4 g, 6.16 mmol) in ethyl acetate (20 ml) was added a solution/suspension of stannous chloride (4.2 g, 22.22 mmol) in HCl (7.5 ml). An immediate yellow colour resulted. Stirring was continued until TLC (A) and ninhydrin development indicated the conversion of starting materials. The acidic solution was made basic by addition of NaOH solution (1M) and then extracted with saturated potassium chloride solution (4×10 ml). The organic layer was dried over sodiumsulphate and purified by column chromatography, eluting with dichloromethane to afford [7] as a yellow/orange solid (500 mg, 38%). Crystallisation from-chloroform afforded [7] as fine orange needles (220 mg). Rf (B) 0.18; δH(400 MHz; Acetone-d6) 2.29 (3H, s, CH3) 8.04 (1H, s, Ar—H) 8.19 (1H, s, Ar—H) 8.39 (1H, s, NOH) 8.42 (1H, s, NOH); m/z (EI−LR) 213 [(M) calc. for C7H7N3O5 213]; (Found C, 38.02; H, 2.07; N, 18.84. C7H7N3O5 requires C, 39.43; H, 3.28; N, 19.72%).

Provenance & Evidence