3-Chloroaniline → HCID 9908998, compound

Participants

Reaction Steps

To a 0° C. solution of acid 6 (141 mg) in 2 mL of dry DMF was added triethylamine (0.089 mL), and 3-chloroaniline (0.046 mL). 1-Hydroxybenzotriazole hydrate (80 mg) was added, followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (106 mg). After six hours, the reaction was poured into EtOAc, washed with sat. aq. NaHCO3 solution and brine, then dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by silica gel chromatography (2-6% MeOH/CH2Cl2) gave a white foam which was taken up in CH2Cl2, treated with 1 M HCl/ether solution, and concentrated in vacuo. The product hydrochloride 1 was isolated as a white powder.

Provenance & Evidence