Synthesis
The general procedure for the synthesis of methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate from methyl 6-quinolinecarboxylate was as follows: carbon-loaded palladium (1.50 g, 10% mass fraction) and ammonium formate (10.5 g, 165 mmol) were added in methanol (20 mL), followed by methyl 6-quinolinecarboxylate (1.20 g, 6.41 mmol). The reaction mixture was stirred at 70°C for 2 hours. Upon completion of the reaction, the synthesis was processed according to the synthesis method of Step 1 of Example 2 to afford the white solid product methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate (1.20 g) in 97.9% yield.
References
[1] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 1981 - 1985
[2] Catalysis Science and Technology, 2018, vol. 8, # 10, p. 2648 - 2653
[3] Patent: CN105524053, 2016, A. Location in patent: Paragraph 0534; 0535; 0536
[4] ACS Catalysis, 2018, vol. 8, # 5, p. 4545 - 4557
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3216 - 3220
