Sodium Bicarbonate → Ethyl 7-bromoisoquinoline-3-carboxylate

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Reaction Steps

To a mixture of ethyl-3-(4-bromophenyl)-2-formamidopropanoate (23.5 g, 78 mmol) in DCM (200 mL) was added (CO)2Cl2 (8 ml, 84 mmol). The reaction mixture was stirred at r.t. for 30 mins. Then the reaction solution was cooled to 0° C. and FeCl3 (16 g, 98 mmol) was added into the solution, followed by stirring at r.t overnight. After the solution was extracted by CH2Cl2, the combined organic layers were concentrated in vacuo to afford a black oil. The oil was dissolved in the EtOH (100 ml), and concentrated H2SO4 was added into the solution and refluxed at 80° C. overnight. The solution was poured into saturated NaHCO3 and extracted by EA. After drying with anhydrous Na2SO4, the solution was concentrated in vacuo, and the residue was purified by silica gel chromatography (PE/EA=8:1 to 5:1) to afford ethyl 7-bromoisoquinoline-3-carboxylate as a yellow solid (5.2 g, yield: 23.8%).

Provenance & Evidence