Uses
3,4,5-Trimethoxybenzoyl Chloride is used as a reagent in the synthesis of 2-methyl-8-(3,4,5-trimethoxybenzamido)-1,2,3,4-tetrahydroisoquinoline and its analogs which display great antihypertensive activity.
Synthesis
The general procedure for the synthesis of 3,4,5-trimethoxybenzoyl chloride from 3,4,5-trimethoxybenzoic acid was as follows: thionyl chloride (13.7 mL, 189 mmol) was added dropwise to a solution of CHCl3 (30 mL) containing 3,4,5-trimethoxybenzoic acid (8.00 g, 37.7 mmol). After the dropwise addition, the reaction mixture was heated to reflux and maintained for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature. Subsequently, the solvent and excess thionyl chloride were removed by distillation under reduced pressure to afford 3,4,5-trimethoxybenzoyl chloride as a colorless oil in quantitative yield. The obtained product can be used in the subsequent reaction without further purification. The characteristic absorption peaks of the infrared spectrum (NaCl) were: νmax/cm-1 2970, 2944, 1750, 1590, 1457, 1415, 1130, 1128.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5864 - 5869
[2] Tetrahedron, 2011, vol. 67, # 25, p. 4601 - 4611
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 20, p. 6042 - 6054
[4] Letters in Drug Design and Discovery, 2018, vol. 15, # 12, p. 1319 - 1328
[5] Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 2, p. 236 - 244
