3-Chlorophenylacetic acid → HCID 14918164, compound

Temperature

0 °C

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).

1. temperatureThe reaction mixture was warmed to room temperature
2. washwashed with saturated NaHCO3 aqueous solution (2 times), 1N HCl aqueous solution (2 times) and brine (2 times)
3. dry with materialdried over anhydrous MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe liquid obtained
7. customwas purified by column chromatography on silica eluting with EtOAc/hexane 1:1

ORD record

ord-0943592db6c942a597cc1bafc97f0f73

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06509336B1