Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthetic route for this compound starting from 4-nitrosalicylic acid. The synthesis involves multiple steps. Specify all the reagents and the reaction conditions it may require in each step.

Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthetic route for this compound starting from 4-nitrosalicylic acid. The synthesis involves multiple steps. Specify all the reagents and the reaction conditions it may require in each step.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.70P

See similar textbooks

Related questions

Q: A Claisen condensation

A: (a)

Q: Propose a synthesis to convert the shown reactants into the shown products. For the first synthesis,…

Q: Following are the final steps in one industrial synthesis of vitamin A acetate. H,SO, ÓH (1) (2) (3)…

A: (a)

Q: Show how acid derivatives are easily interconverted by nucleophilic acyl substitutionfrom more…

Q: Predict the products of the reaction of phenylacetaldehyde and acetophenone with the following…

A: In this question, Predict the products of the reaction of phenylacetaldehyde and acetophenone with…

Q: Propose a mechanism for formation of 2-carbethoxy-4-butanolactone and 4-butanolactone…

A: 2-carbethoxy-4-butanolactone

Q: Which of the following reagents will not undergo a substitution reaction with the benzenediazonium…

A: this a substitution reaction of benzenediazonium chloride salt.

Q: Show how to synthesize the following compound using either the malonic ester synthesis or the…

A: 4-Phenyl-2-butanone: Its common name is benzylacetone. It is flowery in smell. It is prepared by…

Q: Which of the following reagents will not undergo a substitution reaction with the benzenediazonium…

A: Those reagents which show substitution reaction with benzenediazonium chloride salt are given below…

Q: In the Gabriel synthesis of primary amines, N-potassiophthalimide is used as a source of the…

A: This is a Gabriel phthalamide synthesis reaction. Through this reaction 1° amine is produced by the…

Q: Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally…

A: Given reaction,

Q: Given this retrosynthetic analysis, propose a synthesis for the antidepressant moclobemide. CI H CI…

Q: The reagent diisobutylaluminum hydride (DIBALH) reduces esters to aldehydes. When nitriles are…

Q: Show how to synthesize the following amines from the indicated starting materials…

A: Given The given organic compounds are N-butylpiperidine and piperidine.

Q: The following compound used in perfumery has a violet-like scent. Propose a synthesis of this…

A: Organic synthesis is a special branch of chemical synthesis which concerns the systematic…

Q: ČOEt 1. EtO-Na+ OEt 3. NAOH, H,O, heat EtO 4. HCI, heat 2-Carbethoxy- 4-Butanolactone…

Q: Propose a synthesis route to prepare 2‐phenylacetaldehyde starting from benzene:

Q: It is possible to generate sulfur ylides in a manner similar to that used to produce phosphonium…

A: First, the sulfur ylide attacks the carbonyl carbon and forms an intermediate.

Q: Spasmolytol, as its name suggests, is an antispasmodic. Given this retrosynthetic analysis, propose…

A: Spasmolytol is an antispasmodic drug that used to relieve the pain of involuntary muscle. Salicylic…

Q: 2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as…

Q: Propose the reagents and conditions for the following multistep synthesis, one of the steps will be…

Q: Propose a synthesis for 3,5-dichloro-2-methoxybenzoic acid starting from phenol.

A: Synthesis for 3,5-dichloro-2-methoxybenzoic acid from phenol is given as

Q: The synthesis of the following compound involves the use of an epoxide. Describe the retrosynthetic…

A: Under acidic condition ring opening of epoxide occurs from the more hindered site.

Q: Give the shortest route to produce the desired products 1. cyclobutanoic acid to ethyl-cyclobutyl…

A: 1. Cyclobutanoic acid on treatment with SOCl2/pyridine give corresponding acid chloride which on…

Q: [1.] Show the preparation of 2,3-dimethyl-1-pentanol using Acetoacetic Ester Synthesis. [2.] Show…

A: Acetoacetic ester Synthesis is the reaction where ethyl acetoacetate is alkylated at the α-carbon to…

Q: Based on this retrosynthetic analysis, propose a synthesis of the anticoagulant (a substance that…

A: Diphenadione can be produced from the retrosynthetic reaction of diethyl pthalate and the given…

Q: H. エ-Z

Q: Show how to synthesize the following compound using either the malonic ester synthesis or the…

A: Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the…

Q: Propose an efficient synthesis of the following compound using the malonic ester synthesis. Propose…

A: 1. Reaction with mechanism of synthesis

Q: „NH2 .COOH Aniline Benzoic acid Benzoic acid can be prepared from aniline via aryl diazonium ion.…

A: Given : We have to tell how the following conversion will take place.

Q: 4. Show how you might carry out the following transformations using any needed inorganic reagents.…

A: Since you have posted a question with multiple sub-parts, we will solve first three subparts for…

Q: Show how to synthesize the following compound using either the malonic ester synthesis or the…

A: The malonic ester synthesis of 2-Propyl-1,3-propanediol undergoes a nuclophilic attack using strong…

Q: Show how to synthesize 3-nitro-4-propoxybenzoic acid from phenol, C6H5OH and any reagents that you…

A: First, the phenol compound reacts with NaH and I-CH2CH2CH3 results to form following compound A.

Q: When 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester).…

A: 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone.

Q: Propose mechanisms for the nucleophilic acyl substitutions to form ethyl benzoate…

Q: 3 Treatment of 1-aminoadamantane, C„H„N, with methyl 2,4-dibromobutanoate in the presence of a…

A: In the given SN2 reaction, 1-aminoadamantane act as a nucleophile and it make a bond with terminal…

Q: The widely used anticoagulant warfarin (see "Chemical Connections: From Moldy Clover to a Blood…

A: Reagents: A Compound or mixture added to a system to cause a chemical reaction to take place. Aldol…

Q: Propose a mechanism for the acid-catalyzed reaction below:

A: The possible mechanism explained below for this reaction.

Q: Give a reaction equation you could use to prepare an alkylamine from 2-phenyl-pentanoylazide. Show…

Q: Which of the following acid derivatives can be hydrolyzed in water spontaneously without acid or…

A: Acid derivatives mainly gives Nucleophillic acyl substitution reaction, in which the group attached…

Q: Show how you would synthesize 2-phenylethanamine (PHCH2CH2NH2) starting from the following reagents.…

A: In this question, we want to Synthesized the PhCH2CH2NH2 from the starting material ( which have…

Q: On the basis of retrosynthetic analysis, identify starting materials and synthons for the following…

A: The retrosynthesis is generally a process of disconnecting the target molecules into synthetic…

Q: Show how you would synthesize 2-phenylethanamine (PHCH2CH2NH2) starting from the following reagents.…

A: The reactant in d is an amide which can be named 3-phenylpropanamide. The product…

Q: Identify the best reagents to complete the following reaction. H2O pyridine PHCH2OH pyridine PHOH…

Q: Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed 2 of 2 C D G H. un acid catalyst…

A: Answer is given below

Q: NHCH3 cat. H* .CH3 CH3CH2CHO + NH2CH3 The Mannich reaction is one of the few three-component…

A: The step by step mechanism is shown below:-

Q: Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from…

A: The retrosynthetic method is used to predict the starting material from product structure by…

Q: Give TWO reagents to prepare cyclopentanone from adipic acid.

A: Adipic acid is dicarboxylic acid and cyclopentanone is ketone. We have to two reagents for…

Q: Show how the malonic ester synthesis can be used to prepare carboxylic acid A. (Given: the structure…

Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

Step 2

Step 3

Step 4

Step 5

Trending now

This is a popular solution!

Step by step

Solved in 5 steps with 4 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
Provide a retrosynthetic pathway from the following compound. Indicate reagents needed for each transformation...
Amino acids can be prepared by the reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. The reaction to form alanine involves the following steps: Reaction of diethyl acetamidomalonate with sodium ethoxide to form enolate anion 1; The enolate anion acts as a nucleophile in an SN2 reaction with alkyl iodide 2 to form alkylated intermediate 2; Heating in the presence of aqueous acid hydrolyzes both the ester and the amide bonds, and induces decarboxylation to form alanine. Draw the structure of enolate anion 1.
The following set of reactions convert phenylacetylene to butylbenzene. Give the appropriate reagents for each step of the following reaction sequence.
Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.
Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0 °C, followed by treatment with N,N-diethylaniline.
The following compound may be synthesized through alkylation of an appropriate enamine with an alkyl bromide, followed by hydrolysis of the resulting immonium ion. Using this strategy, provide the necessary starting materials for the synthesis. Draw the necessary enamine below.
Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.