Definition
ChEBI: A member of the class of beta-carbolines that is 1,2,3,4-tetrahydro-beta-carboline substituted at position 3 by a carboxy group.
Synthesis
The general procedure for the synthesis of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid from formaldehyde and L-tryptophan was as follows: first, 1-propanesulfonic acid (817 mg, 4 mmol) was mixed with 2.5 M NaOH solution (1.6 mL), and the mixture was stirred at room temperature until it became clear. Subsequently, 37% formalin (4.87 mL) was added to the mixture. The reaction mixture was stirred at room temperature for 2 hours and then refluxed for 3 hours. Upon completion of the reaction, it was neutralized with 2 M HCl solution to pH 5. The precipitate precipitated was filtered, washed sequentially with water and methanol and finally dried under vacuum to afford the target product 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid. The yield of this step was 99% and the product was a colorless solid with a melting point of 302.2-304.6 °C. Mass spectrometry (FAB) analysis showed m/z 217 (M+1, 100%).
References
[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 2, p. 636 - 646
[2] Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 1994, vol. 48, # 5, p. 434 - 438
[3] Patent: CN106432235, 2017, A. Location in patent: Paragraph 0217; 0218
[4] Patent: US2013/178629, 2013, A1. Location in patent: Paragraph 0109
[5] Molecules, 2010, vol. 15, # 11, p. 7775 - 7791