1-Chloro-2,4-Dinitrobenzene → HCID 59799764, compound

Participants

Reaction Conditions

Reaction Steps

Chloro-2,4-dinitrobenzene 1 (1.00 g, 4.937 mmol) was dissolved in anhydrous EtOH (20 mL) in a small argon purged flask and warmed in an oil bath to 40° C. Addition of 2-(1-methylpyrrolidin-2-yl)ethanamine 30 (0.696 g, 5.431 mmol) occurred dropwise. The reaction was stirred at 65-70° C. for 24 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and ethyl acetate and 1M ammonium hydroxide solution added to adjust pH to 10. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with H2O, brine (twice), dried over magnesium sulphate, filtered and then concentrated. Recrystallization of the crude solid from EtOH yielded a yellow powder 31 (2,4-Dinitro-phenyl)-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-amine Yield: 0.979 grams (67.4%). 1H NMR (DMSO) 8-1.51-1.71 (m, 3H), 1.78-1.96 (2×m, 3H), 2.06-2.14 (m, 1H), 2.26 (s, 3H), 2.26-2.36 (m, 1H), 2.93-3.03 (m, 1H), 3.48-3.53 (m, 2H), 7.18 (d, 1H, J=9.6), 8.27 (dd, 1H, J=9.7, 2.7), 8.86 (d, 1H, J=2.8), 9.50 (br s, 1H); MS (ESI): 295 (MH+, 100%)

Provenance & Evidence