Us3819648a us19844271a us3819648a us 3819648 a us3819648 a us 3819648a us 19844271 a us19844271 a us 19844271a us 3819648 a us3819648 a us 3819648a authority us united states prior art keywords phthalimide reaction urea aromatic phthalic acid prior art date 19711112 legal status the legal status is an assumption and is not a legal conclusion. Why cannot aromatic primary amines be prepared by gabriel. This method has been applied to the synthesis of amino acids as well. Jan 12, 20 vii gabriel phthalimide synthesis is preferred for synthesising primary amines. The use of dmf as the solvent generally increases the yield by accelerating the s n 2 reaction. They are hydrophobic and neutral, and can therefore cross biological membranes in vivo. Gabriel phthalimide synthesis mechanism, synthesis of primary. This video is highly rated by class 12 students and has been viewed 2104 times. Saponification of esters gabriel synthesis template synthesis using phthalimide from phys 222 at university of louisville. Gabrielcolman phthalimide rearrangement synthesis of isoquinolines 4, 5 by base catalyzed rearrangement of phthalimides 3. General procedures for synthesis of phthalimide derivatives phethalic anhydride 1 0. Aromatic amines cannot be prepared by gabriel phthalimide synthesis reaction because aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide. Gabriel phthalimide synthesis nitrogen containing compound. This lesson gives an outline of the steps to synthesise primary amines from pthalimide.
Potassium phthalimide is a nh 2synthon which allows the preparation of primary amines by reaction with alkyl halides. Phthalimide is a dicarboximide that is 2,3dihydro1hisoindole substituted by oxo groups at positions 1 and 3. Therefore, gabriel phthalimide synthesis is preferred for synthesizing primary amines. Two methods for the preparation of phthalimide rated as. Saponification of esters gabriel synthesis template synthesis. It involves nucleophilic substitution s n 2 of alkyl halides by the anion formed by the phthalimide. Phthalimide analogues have been extensively used in medicinal chemistry owing to their wide range of applications as anticonvulsant, antiinflammatory, analgesic, hypolipidimic and. All structured data from the file and property namespaces is available under the creative commons cc0 license. Doing a direct s n 2 reaction would result in a quaternary amine salt, which can be pretty useless unless you use hofmann elimination.
Three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. Chemistry assignment help, gabriel phthalimide synthesis nitrogen containing compound, gabriel phthalimide synthesis. Two methods for the preparation of phthalimide, hive novel. The dyeing behaviour and fastness properties of these dyes had been investigated. This method is used in the formation of pure aliphatic. The potassium salt is treated along with an alkyl halide. Dec 30, 2017 three azo dyes had been synthesized using npropyl substituted, dibromosubstituted and dicyanosubstituted phthalimides as diazo components. We also acknowledge previous national science foundation support under grant numbers 1246120. Explain the following reactions i gabriel phthalimide. Gabriel primary amine synthesis major reference works. What is the mechanism of phthalimide synthesis from. Recent advances and future prospects of phthalimide. It involves nucleophilic substitution s n 2 of alkyl halides by the anion formed by the phthalimide but aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide.
Synthesis, characterization, electronic absorption and. It is used as a precursor to other organic compounds as a masked source of ammonia. The gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. A new and onepot version of the gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via. Apr 12, 2020 gabriel phthalimide synthesis full mechanism class 12 video edurev is made by best teachers of class 12. Systematic synthesis of phthalimideprotected unsaturated. It involves the reaction of benzene diazonium salts with phenols or aryl. Phthalimide, when treated with alcoholic potassium hydioxide, is easily converted into potassium phthalimide which on treatment with alkyl halide followed by hydrolysis with acid or alkali yields phthalic acid and a primary amine. On vigorous oxidation, it gives 1,2benzenedicarboxylic acid. Which amines could be made by a gabriel synthesis phthalimide, koh followed by h2nnh2. Request pdf gabriel synthesis synthesis of primary amines using potassium phthalimide and alkyl halides.
After the first hydrolysis, why would the amine be removed in favor of a hydroxyl. The two crops of crystals are united note 4 and washed with 200 cc. A byproduct of the gabriel phthalimide synthesis of. For the love of physics walter lewin may 16, 2011 duration. Gabriel phthalimide synthesis is preferred for synthesising. Synthesis and application of phthalimide disperse dyes. Strategic applications of named reactions in organic synthesis. Gabriel phthalimide synthesis results in the formation of primary amine only. Jan 14, 2016 viigabriel phthalimide synthesis is preferred for synthesizing primary amines.
Our team of scientists has experience in all areas of research including life science, material science, chemical synthesis, chromatography, analytical and many others. Reaction of phthalimide with koh removes the nh proton giving an imide ion, a good nucleophile. In the following molecule, which hydrogen atom is most susceptible to abstraction by free radicals. These metrics are regularly updated to reflect usage leading up to the last few days. Distinction indication of colour, smell, precipitates 4. Media in category gabriel synthesis the following 39 files are in this category, out of 39 total. The first technique often produces low yields or side products. Phthalimides prepared under ball milling conditions were used in a. Gabriel synthesis of hexakisaminomethylbenzene and its derivatization junya masuda department of chemistry, faculty of science, shizuoka university, 836 ohya, surugaku, shizuoka, 4228529 japan. When treated with various halogen containing compounds, it is alkylated in a manner quite similar to that observed in the alkylation of ammonia and of amines even though phthalimide is by no means an amine. Synthesis, characterization, electronic absorption and antimicrobial studies of nsilatranylpropylphthalimide derived from phthalic anhydride author links open overlay panel gurjaspreet singh a amandeep saroa a shally girdhar a sunita rani a subash sahoo a duane choquesillolazarte b.
Phthalimide on treatment with ethanolicpotassium hydroxide forms potassiumsalt of phthalimide which on heating with alkyl halide followed by alkaline hydrolysis produces the corresponding. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. Gabriel phthalimide synthesis mechanism, synthesis of primary amine scope application jam net gate. It is used for the preparation of primary aliphatic amines. Therefore, gabriel phthalimide synthesis is preferred for synthesising primary amines. Gabriel synthesis of hexakisaminomethylbenzene and its. Before we get into the mechanism, lets look at the reaction pathway. In organic chemistry, imide is a functional group consisting of two carbonyl groups bound to nitrogen. Gabriel synthesis generally fails with secondary alkyl halides. Synthesis and bioactivity of novel phthalimide derivatives. The gabriel synthesis of primary amines free download as pdf file. Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines. Alkylation of phthalimide gabriel synthesis of primary alkyl amines reaction type. Gabriel phthalimide synthesis involves a chemical reaction where primary alkyl halides are transformed into primary amines.
It also covers the process of synthesis of pthalimide itself. Pdf file of the applications of gabriel amine synthesis. The absorption maxima of the dyes were observed in the range 360 to 700. Nomenclature alphabetical order of name of side chain, use of comma and hyphen. A fourstep route for the synthesis of novel phthalimideprotected hydrazine heterocycles that include a c. Gabriel synthesis potassium phthalimide is a secondary diamide that can yield primary amines in much better yield when treated with 1.
Gabriel phthalimide synthesis is preferred for the. Gabriel phthalimide synthesis mechanism, synthesis of. This reaction is known as the gabriel synthesis of primary amine. The potassium salt is the reagent used in the gabriel synthesis. Phthalimide is first treated with koh to obtain potassium phthalimide which is then treated with alkyl iodide. The phthalimide has been reported to be easily deprotonated by koh or naoh because of the two electron. Bonus question is why does wikipedia list a slightly different reaction. Recent advances in the chemistry of phthalimide analogues and. An unprecedented approach to the gabriel amine synthesis utilizing. The synthesis is used to get primary amines from primary alkyl halides and is named after the german scientist siegmund gabriel. Hydrolysis of the phthalimide ring was found to be largely influenced by steric effects rather than inductive effects.
What links here related changes upload file special pages permanent link page information. Gabriel phthalimide synthesis full mechanism class 12. Zeglam 1, asma eswayah 1, jamal baki 1, esra alnnas 1, yousra haroon 1, majda zitouni 1 and wafa sdera 1. Understanding the mechanism of gabriel phthalimide synthesis. Rapid and clean synthesis of phthalimide derivatives in. Pdf synthesis of phthalimide derivatives as potential. What is the mechanism of phthalimide synthesis from phthalic. Gabriel phthalimide synthesis results in the formation of 1 amine only. Citations are the number of other articles citing this article, calculated by crossref and updated daily.
Find an answer to your question gabriel phthalimide synthesis is preferred for synthesising primary amines. Bromo substituted dyes have the lowest rates of hydrolysis. After alkylation, the phthalimid is not nucleophile and does not react anymore. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an s n 2 fashion to give an nalkylphthalimide intermediate. An unprecedented approach to the gabriel amine synthesis. Basically, the protocol also offers a powerful tool fo. Phthalimideprotected bochydrazine was used as a starting material, which was. The gabriel synthesis is an organic reaction used to convert an alkyl halide to a primary amine using phthalimide with base and followed by hydrazine. Pdf synthesis of some nphthalimide amino acids derivatives. Structure of phthalimide phthalimide is an imido derivative of phthalic acid. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh.
All of the synthesized intermediates and dyes have been characterized by ms, 1hnmr and ir analyses. Gabriel phthalimide synthesis gabriel synthesis is used for the preparation of primary amines. The gabriel synthesis of primary amines amine ester scribd. This lesson covers the reaction mechanism for gabriel pthalimide synthesis. The goal of gabriel synthesis is to create a primary amine rnh 2. A variety of phthalimide derivatives have been synthesised effectively in hightemperature, highpressure h2oetoh mixtures hthph2oetoh as the solvent. Asian journal of pharmaceutical analysis and medicinal chemistry. Grignard reagent, gabriel phthalimide cbse class 12 xii. But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide. Pdf new modification of gabriel reaction in synthesis of primary.
The gabriel synthesis is a great way to make primary amines. Product is cleaved by reaction with base or hydrazine, which leads to a stable cyclic product. Potassium phthalimide is a nh2synthon which allows the preparation of primary amines by reaction with alkyl halides. A very neet way of preparing primary amines is by using gabriel synthesis. Gabriel phthalimide synthesis mechanism has 3 steps. Reaction of potassium phthalimide with halogenoalkanes and with a variety of other alkylating agents leads. Nucleophilic substitution then nucleophilic acyl substitution summary. Name reactions name of reagent, temperature and balancing of the equation 3. A new and onepot version of the gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. Files are available under licenses specified on their description page. The reaction is named after the german chemist siegmund gabriel, who first posited the synthesis with the aid of his partner, james dornbush. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext.
Two methods for the preparation of phthalimide, hive. Jun 15, 2015 3 answers to 14 gabriel phthalamide synthesis is used in the preparation of a primary alphatic amines b primary aromatic amines c secondary amines d pure primary aliphatic or aralkyl amine i think the ans is a but im confused with a and d cn u say wic is the right ans. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. This clean method is based on the condensation of ophthalic acid and amines and affords phthalimide compounds as pure crystals in most cases, because of. Pdf 1 nsubstituted imides are formed during the telomerization of 1,3dienes with phthalimide by the action of homogeneous palladium catalysts of the. Phthalimide is alkylated with alkyl or benzyl halide and then hydrolysed or hydrazinolysis to get pure primary. The gabriel synthesis is a threestage procedure used to prepare primary aliphatic amines from the corresponding organic halides eg. Traditionally, the reaction uses potassium phthalimide. Solved 14 gabriel phthalamide synthesis is used in the.
The alkylation involves copper catalysed carbene insertion into the nh bond of phthalimide. This alkylation procedure doesnt produce ammonium salts like the s n 2 reaction would. Therefore,gabriel phthalimide synthesis is preferred for synthesizing primary amines. The gabriel synthesis is a threestage procedure used to prepare primary aliphatic amines from the corresponding organic halides. The gabriel synthesis involves the reaction of the conjugate base of phthalimide and an alkyl halide to give an alkyl phthalimide which is subsequently hydrolyzed to the primary alkyl amine. Gabriel phthalimide synthesis mechanism explanation and. Compared with stype dyeing disperse dyes, phthalimide dyes have lower dyeing rates and lower levelness of dye migration. The yield of airdried potassium phthalimide is 160180 g.
It involves the treatment of phthalimide with ethanolic potassium hydroxide to form potassium salt of phthalimide. The synthesis of primary amines by way of alkylation of phthalimide is called the gabriel amine synthesis. The advantage of this method is that over alkylation is avoided see previous page. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. For these reasons, other methods for liberating the amine from the phthalimide have been developed. Recent advances in the chemistry of phthalimide analogues.
Pdf file of the applications of gabriel amine synthesis name. Potassium phthalimide is treated with base, then a primary alkyl halide, and then either hydrazine, acid, or base. Phthalimide is reacted along with koh to form potassium phthalimide. Synthesis of some nphthalimide amino acids derivatives and evaluation their biological activity article pdf available in international journal of chemtech research 84. The synthesis of 4a, 4b and 6a6e is described as follows. It is used as a precursor to other organic compounds as a. Recent advances and future prospects of phthalimide derivatives. This method is used in the formation of pure aliphatic primary amines. Then alkyl phthalimide on hydrolysis yields alkylamine.
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