2-Chloro-N-(2-methoxy-4-nitro-phenyl)-acetamide synthesis
- Product Name:2-Chloro-N-(2-methoxy-4-nitro-phenyl)-acetamide
- CAS Number:67291-72-9
- Molecular formula:C9H9ClN2O4
- Molecular Weight:244.63
Yield:67291-72-9 85%
Reaction Conditions:
Stage #1: 2-methoxy-4-nitrophenylaminewith triethylamine in tetrahydrofuran at 0; for 0.166667 h;
Stage #2: chloroacetyl chloride in tetrahydrofuran at 20; for 12 h;
Steps:
Procedure for the Preparation of 2-Chloro-N-(2-methoxy-4-nitrophenyl)acetamide (4)
To a solution of 2-methoxy-4-nitrophenylamine (2.0 g,11.9 mmol) in THF (30 mL), triethylamine (6.8 mL, 47.6mmol) was added and the mixture was stirred for 10 min at 0°C. Chloroacetyl chloride (1.5 mL, 20.0 mmol) was then slowly added. The reaction solution was stirred at room temperaturefor 12 h, then the solvent was removed and the residue was poured into cold water (50 mL). The precipitate was collected by filtration to give the compound 4. Yield 85.0,1H NMR (400 MHz, CDCl3): 9.18 (br s, 1H), 8.53 (d, J =9.0 Hz, 1H), 7.90 (dd, J = 9.0, 2.4 Hz, 1H), 7.76 (d, J = 2.4Hz, 1H), 4.23 (s, 2H), 4.03 (s, 3H). ESI-MS m/z: 245.1[M+1]+. The data are accordance with the literature [19].
References:
Wang, Jianhong;Cheng, Pengfei;Luo, Tianwei;Wang, Zhaoyi;Zhang, Yahong;Zhao, Jin [Medicinal Chemistry,2014,vol. 10,# 5,p. 506 - 511]