N,N-Dimethylethylenediamine → HCID 17611030, compound

Participants

Reaction Steps

To a chilled solution (−10° C.) of 4-chloro-3-nitrobenzoyl chloride (0.92 g, 4.2 mmol) in anhydrous THF (20 mL) added dropwise a solution of N,N-dimethylethylenediamine (0.44 mL, 4.0 mmol) in THF (20 mL). After stirring 30 min combined with a 1:1 mixture of ice and saturated NaHCO3 (50 mL) and then extracted with EtOAc (3×80 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated and chromatographed (silica gel, MeOH/DCM, 3:22) to yield the title compound (0.40 g, 37%) as a pale yellow solid. 1H-NMR (CDCl3): δ 8.28 (1H, d), 7.96 (1H, dd), 7.63 (1H, d), 6.98 (1H, br s), 3.54 (2H, m), 2.56 (2H, t), 2.30 (6H, s)

Provenance & Evidence