Synthesis of carboline

Synthesis of carboline - The melting point was also...

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Synthesis of 1, 2, 3, 4-Tetrahydro-B-Carboline Performed on 7/27/10 Results: Tryptamine (.241g) was reacted with water and glyoxilic acid (.124g) to form the intermediate product. This product has a weight of .569g and was then reacted with HCL (2mL) and potassium hydroxide before being refluxed to create the desired product tryptoline at pH 12. The collected product had a weight of .003g, giving a percent yield of1.16% The melting point was found to be 193.2-198.1°C. Discussion: This reaction was not very successful. The percent yield was less than satisfactory due a large amount of the product lost at each step. The biggest loss most likely occurred when the second product was washed with water. The product was soluble in water at this point and a large portion of the solid was lost in the rinsing process. Another problem was that during the reflux process, not much of the product precipitated out of solution. This led to an already low yield even before the washing.
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Unformatted text preview: The melting point was also slightly lower than expected, leading me to believe that the product was contaminated, possibly with water. This was due to lack of drying after the rinsing process and there was not enough product left to conduct a second melting point after further drying. The synthesis of B-carboline involves three distinct steps that can be seen here: Based on this arrow-pushing mechanism and the second step where 3M HCl was added, the reaction-coordinate diagram for this step was determined below: Conclusion: From this reaction it can be seen that proper lab techniques are crucial to proficient outcomes. In this reation knowledge of miscibility and acid, base chemistry are key for success. Questions: 1. The ionic product: 2. The initial step leading to each of the products: 3. The role of the HCl in the decarboxylation step is to protonate the product and stabilize the reaction. 4. The expected product:...
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Synthesis of carboline - The melting point was also...

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