3-Chlorophenylacetic acid → HCID 14918164, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-chlorophenylacetic acid (5.00 g, 29.3 mmol), 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide HCL (6.18 g, 32.2 mmol), and 1-hydroxybenzotriazole (HOBt; 4.00 g, 29.3 mmol) in dichloromethane (DCM; 40 mL) was stirred at room temperature for about 10 minutes. The solution was cooled to about 0° C. To it were added N,O-dimethylhydroxylamine HCl (2.86 g, 29.0 mmol) and diisopropylethylamine (DIEA; 3.80 g, 29.3 mmol). The reaction mixture was warmed to room temperature and stirred for about 5 hours. The solution was diluted with 100 mL of DCM and washed with saturated NaHCO3 aqueous solution (2 times), 1N HCl aqueous solution (2 times) and brine (2 times), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The liquid obtained was purified by column chromatography on silica eluting with EtOAc/hexane 1:1. The title compound was obtained as colorless liquid. Yield: 5.60 g, 89%. Rf=0.44 (silica, EtOAc/hexane 1:1). 1H NMR (300 MHz, CDCl3) 7.18-7.34 (m, 4H), 3:76 (S, 2H), 3.66 (S, 3H), 3.22 (S, 3H).

Provenance & Evidence