Benzoyl chloride, 3-nitro- → HCID 883681, compound

Participants

Reaction Steps

N,N-Dimethylethylendiamine (14.25 g, 61.0 mmol) was added dropwise into a solution of commercially available 3-nitrobenzoyl chloride (25.0 g, 134 mmol) in dry THF (150 mL) at 0° C. and stirred for 45 min. The reaction mixture was evaporated to under reduce pressure to dryness and residue was recrystallized from EtOH to give N-(2-dimethylaminoethyl)-3-nitrobenzamide; 31.0 g (97%); mp 89-90° C.; 1H NMR (CDCl3) δ 2.29 (6H, s, 2×Me), 2.57 (2H, t, J=5.8 Hz, CH2), 3.57 (2H, q, J=5.6 and 5.8 Hz, CH2), 7.37 (1H, brs, exchangeable, NH), 7.63 (H, d, J=7.9 Hz, ArH) 8.19 (1H, m, ArH), 8.33 (1H, m, ArH), 8.66 (1H, s, ArH). Anal. Calcd. for (C13H21N3O3): C, 58.41, H, 7.92, N, 15.72. Found: C, 58.23, H, 7.69, N, 15.90.

Provenance & Evidence