Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 32024-15-0, name is 3-Iodo-4,5-dimethoxybenzaldehyde, A new synthetic method of this compound is introduced below., SDS of cas: 32024-15-0
7-Ethoxy-4-(3-iodo-4,5-dimethoxybenzyl)isoquinolin-8-ol hydrochloride 72In an ace pressure tube, 2-((2,2-diethoxyethylamino)methyl)-6-ethoxyphenol SAO 33014 (244 mg, 0.86 mmol) and 3-iodo-4,5-dimethoxybenzaldehyde RBO 40110 (250 mg, 0.86 mmol) were dissolved in a mixture EtOH:37% HCI solution = 1 :1 (10 ml_). The reaction mixture was stirred at 100C for 10 min then cooled to RT. The volatiles were removed under vacuum and the residue was taken back in EtOAc (150 ml_) and neutralized with a 10% NaHCO3 aq. solution (15 ml_). The separated organic layer was washed with water (3×30 ml_), brine (30 ml_), dried over Na2SO4, filtered and evaporated to give a yellow solid. This solid was purified by column chromatography (SiO2, eluent CH2CI2:EtOAc = 100:0 to 50:50) to give, after evaporation and drying, 7-ethoxy-4-(3-iodo-4,5-dimethoxybenzyl)isoquinolin-8-ol (37 mg). This solid was dissolved in MeOH (2 ml_) and a 0.49 N HCI solution in MeOH (160 muIota_, 0.08 mmol) was slowly added. The reaction mixture was stirred at 4C for 15 min. After evaporation and drying under P2O5, 7-ethoxy-4-(3-iodo-4,5- dimethoxybenzyl)isoquinolin-8-ol hydrochloride 72 (39 mg, 9% yield) was obtained as a yellow solid. MW: 501 .75; Yield: 9%; Yellow Solid; Mp (C): 221 .9Rf. 0.40 (CH2CI2:EtOAc = 50:50, free base).1H-NMR (CD3OD, delta): 1 .50 (t, 3H, J = 9 Hz, CH3), 3.75 (s, 3H, OMe), 3.81 (s, 3H, OMe), 4.35 (q, 2H, J = 9 Hz OCH2), 4.47 (s, 2H, CH2), 7.00 (s, 1 H, ArH), 7.23 (s, 1 H, ArH), 7.82 (d, 1 H, J = 9 Hz, ArH), 8.03 (d, 1 H, J = 9 Hz ArH), 8.09 (s, 1 H, ArH), 9.66 (s, 1 H, ArH).13C-NMR (CD3OD, delta): 15.0 (CH3), 35.9 (CH2), 56.5 (O-CH3), 60.7 (O-CH3), 66.9 (O- CH2-CH3), 93.1 , 1 15.0 (ArH), 1 16.5 (ArH), 120.5, 126.8 (ArH), 128.4 (ArH), 131 .6 (ArH), 132.6, 137.3, 137.4, 142.8 (ArH), 146.5, 147.0, 149.3, 154.2.MS-ESI m/z (% rel. Int.): 466.0 ([MH]+, 100).HPLC: Method A, XBridge column, detection UV 254 nm, RT = 4.68 min, peak area 99.0%.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; EXONHIT S.A.; LEBLOND, Bertrand; TAVERNE, Thierry; BEAUSOLEIL, Eric; CHAUVIGNAC, Cedric; CASAGRANDE, Anne-Sophie; DESIRE, Laurent; WO2011/151423; (2011); A1;,
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