Isoquinolone Synthesis Lab Report
Guimond and Fagnou et al disclosed an intermolecular and mechanistically distinct approach for the synthesis of the isoquinolone motif 1.46 via Rh(III)-catalyzed annulation of benzhydroxamic acids 1.45 with alkynes (Scheme 1.13).20 This reaction proceeds in the absence of any external oxidant and N-O bond in the hydroxamic acid is utilized for the C-N bond formation. In the case of meta-substituted benzhydroxamic acids, annulation occur regioselectively at the less hindered side. Both symmetrical and unsymmetrical alkynes successfully coupled with benzhydroxamic acids. The synthesis of isoquinolones from benzamides and alkynes in the presence of rhodium complex was reported by Rovis et al (Scheme 1.14) also.21 In this reaction, Cu(OAc)2.H2O …show more content…
Pioneering work by Ackermann et al disclosed that less expensive ruthenium complex also can catalyze the isoquinolone synthesis from benzamides with alkynes.24 The reaction of N-substituted benzamides with internal alkynes in the presence of [RuCl2(p-cymene)]2 with Cu(OAc)2.H2O as an oxidant afforded isoquinolones with good substrate scope (Scheme 1.17). The reaction works well with both symmetrical and unsymmetrical alkynes, and in case of unsymmetrical alkynes highly regioselectivity was achieved. Following this report, the same group discovered a green protocol for the synthesis of isoquinolones from N-methoxybenzamides in water (Scheme 1.18).25 In this reaction, carboxylate salts are used as additives along with the ruthenium complex. The green protocol was viable with free hydroxamic acids also. Li et al also reported the synthesis of isoquinolone motif using N-methoxybenzamides 1.60 under mild reaction conditions in the presence of ruthenium catalyst without using any external oxidant.26 Here C-H bond functionalization occurs at room …show more content…
Some bidentate directing groups also used for these heterocyclic syntheses. Chatani et al discovered a nickel catalyzed synthesis of isoquinolones from aromatic amides containing 2-pyridylmethylamine moiety 1.72 by oxidative cycloaddition with alkynes (Scheme 1.23).32 The reaction proceeds via coordination of amide 1.72 to the nicker center in a N,N-fashion and forms a cyclometallated complex. Insertion of alkyne into this ortho-metalated complex, followed by reductive elimination afforded the
Grignard Reaction Lab
397 Words | 2 PagesGrignard is a reaction that is crucial to forming the new carbon-carbon bond. This is a two-part lab that teaches new techniques; the purpose of this lab is to introduce realistic organic synthesis and apply acid workup to produce triphenylmethanol. A Grignard reaction is characterized by the addition of a magnesium halide (an organomagnesium halide) to an aldehyde or a ketone in order to form a secondary or tertiary alcohol. These reactions are helpful because they serve as a crucial tool in performing important carbon-carbon bond-forming reactions (Arizona State University, 2018). This experiment aimed to observe the mechanisms of a Grignard reply to synthesize triphenylmethanol from benzophenone using phenylmagnesium bromide as the Grignard reagent.
Isopentyl Acetate Synthesis Lab Report
539 Words | 3 PagesIn this laboratory experiment, 3.030 g of Isopentyl Acetate was synthesized and formed by the esterification of acetic acid with Isopentyl Alcohol. 1.0 mL of Sulfuric acid was used as a catalyst in the reaction. The excess Isopentyl Acetate was used to shift the reaction to the right for esterification to occur. During the extraction, the excess of acetic acid and Isopentyl alcohol was extracted with sodium bicarbonate, and further purification of the Isopentyl acetate was done after through drying with anhydrous sodium sulfate and through simple distillation. The percent yield of the Isopentyl Acetate was 46.6 percent with a theoretical yield of 6.502g. In this laboratory experiment the acetic acid was in excess and the Isopentyl Alcohol was the limiting reagent,
Alkyl Bromide And Ketone Lab Report
843 Words | 4 PagesThe purpose of this experiment was to identify the unknown alkyl bromide and ketone using a Grignard reaction and IR spectrum. Also, retrosynthesis analysis was used to determine the success of identifying starting material. The organometallic compounds have a carbon-metal bond that is used to create alcohol and to expand chains of carbons. Grignard reagents, a part of organometallic ionic compounds, are widely used in organic synthesis because they are considered strong base, strong base carbon nucleophile, and soluble in many organic solvents. Results: Alkyl bromide #24 and alkyl ketone
Isopentyl Acetate Synthesis
1938 Words | 8 PagesIntroduction The purpose of the experiment was to synthesize and purify isopentyl acetate or banana oil. In order to perform this reaction, the mixture containing excess acetic acid and isopentyl alcohol was heated under reflux. The methods of extraction, drying, and distillation were then used to help purify the isopentyl acetate. After the completion of all these processes, we were able to determine the yield and analyze our isopentyl acetate.
Isopentyl Acetate Synthesis Lab Report
626 Words | 3 PagesAbstract During this experiment we will produce Isopentyl Acetate via the fisher mechanisms. The alcohol group is converted into an ester giving off a banana scent. This reaction does not favor the products therefore we must add an excessive amoinut of Acetic Acid to shift the equilibrium to favor the products. Our results showed a successful reaction by comparing our boiling results and infrared results to the textbook data on Isopentyl Acetate. Introduction Isopentyl Acetate is an ester that is commonly referred to as banana oil, this is due to the similarity in odor of bananas.
Benzocaine Synthesis Lab Report
536 Words | 3 PagesThe reaction to synthesize benzocaine was known as a Fisher esterification reaction. The Fisher esterification was reaction between alcohol and carboxylic acid in the presence of acid. The reaction was used to form an ester. In the experiment, sulfuric acid acted as a catalyst and necessary for this reaction to occur. There was a change between the –OH group of carboxylic acid to an –OCH2CH3 group in the reaction.
The Determination Of The Molar Equation For The Reaction Between 1a And 3 Diketene
404 Words | 2 PagesIn our initial experiments, a 19% yield of 3,4-dicarbonyl substituted furan 3a was obtained when α,β-unsaturated carbonyl (1a) and 1,3 diketone (2b) were employed for the reaction (Table 1, entry 1) in a 1:2 molar ratio in the presence of 10mg of CuO-NPs in EtOH at room temperature without any oxidizing agent. When molar ratio of the reactants 1a and 2b were increased to 1:3, an improvement in the yield to 28% was observed (Table 1, entry 2) and molar ratio 1:5 gives the highest yield in the same reaction conditions 38% (Table 1, entry 3). The polar solvent such as DMF, DMSO, H2O, Xylene also gave the desired products but in low yield, while no reactions occurred in acetonitrile, toluene (Table 1, entries 4−9).When we employed a mixture of solvent EtOH: H2O (4:1) slight increase of yield 46% was obtained (Table 1, entry 10), increasing the mixture of solvent ratio to 2:1give the yield 51% (Table 1, entry 11) and solvent ratio 1:1 give the highest yield 60% (Table 1, entry 12).
Synthesis Of 3-Nitrochalcone Lab Report
391 Words | 2 PagesNext, the oxygen is protonated from the 3-nitrobenzaldehyde, which is then followed by an elimination reaction where this acts as a leaving group. The product is the trans-alkene present in the product. After the reaction was completed, purification of the product was conducted using semi-microscale recrystallization.
Benzocaine Synthesis
200 Words | 1 PagesIn the experiment, the primary initial chemical used was a 2.019 g mixture of benzocaine, and benzoic acid. Furthermore, the outcome of the experiment was 0.310 g of pure benzocaine, and 0.145 g of pure benzoic acid. Therefore, the percent recovery of the benzocaine and benzoic acid compounds was found to be 15.35%, and 7.18% respectively. In addition, later on in the process the melting points of the pure compounds were measured. The data of the benzocaine received from the lab was 93.2˚C, which is extremely close to the one reserved in literature (89˚C).
Nucleophilic Substitution Lab Report
1631 Words | 7 PagesNucleophilic Substitution: Preparation of 1-Bromobutane & Alkyl Halide Classification Tests Reference: Experimental Organic Chemistry: A Miniscale and Microscale Approach 6th ed. , by Gilbert and Martin, Chapter 10 and Chapter 14 Discussion: The purpose of this experiment is to look deeper into the nucleophilic substitution bi-molecular conversion of a primary alcohol, 1-butanol, into a primary bromoalkane, 1-bromobutane, using hydrobromic acid from the reaction between sodium bromide and concentrated sulfuric acid. The strong acids allow for the protonation of the basic hydroxyl functional group, to convert it to a good leaving group for the substitution.
Methyl Trans-Cinnamate Lab Report
1399 Words | 6 PagesIt is understood the mechanism is acid-catalyzed where protons coordinate with the carbonyl oxygen to make the carbonyl carbon more electropositive for nucleophilic attack (Scheme 1). In the experimental procedure all reactants were added together, this is inefficient as the protons can coordinate with either trans-cinnamic acid or methanol. Coordination with methanol is unnecessary as it reduces its nucleophilicity and makes less protons available to coordinate with the carboxylic acid. To improve
How Can Cyclooctyne Effectively Reaction With A Vinylketene Complex
131 Words | 1 PagesThe major research question of my studies is if cyclooctyne can be successfully reacted with a vinylketene complex using a cost-effective methodology and in producing a distinct organic complex. In this experiment, a tricarbonyl iron(0) vinylketene complex was reacted with cyclooctyne in a cycloaddition reaction. The method used in this experimentation was based on the fundamentals of Click Chemistry. Since, reactions designed according to the concepts of Click Chemistry produced inoffensive byproducts and high yields, it was hypothesized that this reaction would produce a new methodology in how to synthesize cyclooctyne reacted complexes and produce an unknown organic complex. The primary goal in this research was to form an unknown* complex
Hydroquinone Study
1068 Words | 5 PagesThe hydroquinone metabolite purified from B. methylotrophicus MHC10 was evaluated for its antibacterial activity against a panel of several Gram-positive and Gram-negative bacterial pathogens. The zone of inhibition was used to evaluate the antagonistic activity of the metabolite. The standard antibiotics Ampicillin and Gentamycin were used as the positive control. Both antibiotics showed high antagonistic activity against all test pathogens. But in the case of P. aeruginosa, the hydroquinone treatment showed little high zone of inhibition than ampicillin Lee et al.
Tans-Atovaquone
797 Words | 4 Pages1998) of the parasitic cells. The quinine group of ubiquone gets reduced to the quinol and helps in transferring the electron through an oxidation reduction cycle (Tielens A G M and Hellemond J J V 1998; Kroger A. and Gwith M K 1973). Atovaquone too has a quinine group and thus, it can mimic ubiquone and binds selectively to the Q0 site of parasitic mitochondria thereby block the parasitic mitochondrial respiration (Ridley R G 2002). In the present study, we report binding characteristics of trans and cis-isomers of atovaquone with cytochrome bc1 of yeast using docking technique in order to address the basic question, why trans isomer of atovaquone has much higher drug potency than that of its cis isomer?
Benzoic Acid Lab Report
767 Words | 4 PagesAbstract The unknown concentration of benzoic acid used when titrated with standardized 0.1031M NaOH and the solubility was calculated at two different temperatures (20◦C and 30◦C). With the aid of the Van’t Hoff equation, the enthalpy of solution of benzoic acid at those temperatures was determined as 10.82 KJ. This compares well with the value of 10.27KJ found in the literature.
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