Below i introduce to you two methods for production of phthalimide a reagent that is universaly used for gabriel synthesis. Asian journal of pharmaceutical analysis and medicinal chemistry. Two methods for the preparation of phthalimide, hive. Phthalimide is a dicarboximide that is 2,3dihydro1hisoindole substituted by oxo groups at positions 1 and 3. Nodulation factors are lipooligosaccharides that are secreted by bacteria which trigger the early steps in the formation of root nodules in leguminous plants. The first technique often produces low yields or side products. Citations are the number of other articles citing this article, calculated by crossref and updated daily. I made some phthalimide a couple years ago by three different methods. Naoh or hydrazine to form aliphatic primary amines. After alkylation, the phthalimid is not nucleophile and does not react anymore. The preparation of 42aminoethyl3,5dimethylpyrazole from 42chloro and. Phthalimide on treatment with ethanolic potassium hydroxide forms potassium salt of phthalimide which on heating with alkyl halide followed by alkaline hydrolysis produces the corresponding primary amine. Frequent shaking is necessary, and the sublimed material must be pushed back occasionally into the reaction flask. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is.
Phthalimide article about phthalimide by the free dictionary. Rao and others published preparation of isatoic anhydride from phthalimide find, read and cite all the research you need on researchgate. Solution processing was achieved by preparing a precursor molecule bearing tert. The invention relates to a process for the continuous preparation of phthalimide by reacting phthalic anhydride with ammonia in about the stoichiometric ratio, in a mixing apparatus and subsequently in a reaction tube at a particular flow velocity and a particular temperature. The phthalimide obtainable by the process of the invention is a valuable starting material for the preparation of dyes, pesticides and pigments. A convenient, efficient, and selective nalkylation of nacidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. Synthesis, spectral characterization and ligation of n2. Tcp and phthalimideprotected npentenyl glucosaminide. A new method for preparing 15nlabeled phthalimide from the reaction between phthalic anhydride and 15nurea 99. In the gabriel synthesis, potassium phthalimide is reacted with an alkyl halide to produce an n.
What is the mechanism of phthalimide synthesis from. Preparation of phthalimide by ammoxidation of oxylene and. Synthesis of anthranilic acid from phthalic anhydride. Yep, the same stuff as clorox bleach but twice as strong and several times less expensive. In a process for the preparation of phthalimide by reaction of phthalic acid or anhydride with urea, the improvement comprising contacting the phthalic acid or anhydride with urea in the presence of a liquid aromatic reaction medium in which the urea is substantially insoluble and in which the phthalic acid is slightly soluble. The phthalimide alkylation mentioned in the reading is also known as the gabriel synthesis. Goyazensolide, a biologically active natural product classified as a furoheliangolide, was transformed in a phthalimide derivative that showed an enhanced biological activity against tripanosoma cruzi. A very neet way of preparing primary amines is by using gabriel synthesis. The phthalimide moiety serves as a protected form of ammonia.
The potassium salt is the reagent used in the gabriel synthesis. Phthalimide and nsubstituted phthalimides are an important class of compounds because they possess important biological activities including antiinflammatory activity 1, analgesic activity 2 and hypolipidemic activity 3, and also it is used in organic synthesis and other industrial fields such as in drugs synthesis for the. This method is used for the preparation of primary amines. For these reasons, other methods for liberating the amine from the phthalimide have been developed. Title the reaction between urea and phthalic anhydride. It has now been discovered that phthalide can be prepared by the caustic reduction of phthalimide employing such metals as aluminum, cadmium, magnesium, tin and zinc without employing copper or an inorganic copper salt. Phthalimide, as an important intermediate of organic synthesis, has been prepared with high yield by ammoxidation of oxylene over silicasupported vanadiumchromium oxide catalysts. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Pdf preparation of isatoic anhydride from phthalimide. These metrics are regularly updated to reflect usage leading up to the last few days. The annealed film is transparent to visible light, with an absorption edge of 339 nm. Preparation of anthranilic acid this compound, oaminobenzoic acid, or aniline2carboxylic acid, is usually prepared, per vogel, from phthalimide by treatment with hypobromite or hypochlorite.
The phthalimide carbonyls increase the acidity of the nitrogen thus allowing formation of its conjugate base. Analytical method the separation of the reaction product is carried out accor ding to the methodsl of a. Metals solution of lead acetate pbch 3 coo 2, cobalt chloride cocl 2. The subsequent procedure is the same as when aqueous ammonia is used. I didnt have much time to do chemistry on spring break, unfortunately, but i did get to make some anthranilic acid based on chemplayers video. Recent advances and future prospects of phthalimide. Most importantly, the phthalimide carbonyls protect the nitrogen from over alkylation thus preventing the formation of quaternary ammonium salts. Gabriel synthesis generally fails with secondary alkyl halides. In this manner, phthalimide, indole, benzimidazole, and succinimide can be successfully alkylated.
Two methods for the preparation of phthalimide rated as. Product is cleaved by reaction with base or hydrazine, which leads to a stable cyclic product. Before you read the section on reductive amination you may wish to remind. Tcp and phthalimideprotected npentenyl glucosaminide npg precursors have been utilized in a convergent stereocontrolled synthesis of the nodulation factor nodrfiii c18.
Nitriles can be reduced by lithium aluminum hydride liaih 4 to primary amines. A process for the continuous preparation of phthalimide by reacting phthalic anhydride with ammonia in about the stoichiometric ratio, in a mixing apparatus and subsequently in a reaction tube at a particular flow velocity and a particular temperature. In our work we coupled namino phthalimide with different aldehydes and acid halides to form. Us2919282a us351521a us35152153a us2919282a us 2919282 a us2919282 a us 2919282a us 351521 a us351521 a us 351521a us 35152153 a us35152153 a us 35152153a us 2919282 a us2919282 a us 2919282a authority us united states prior art keywords phthalimide mixture phthalide process zinc prior art date 19530427 legal status the legal status is an assumption and is not a. Synthesis of anthranilic acid and phthalic anhydride. Mix phthalic anhyde 10 g and urea 2 g in a 250 ml rbf. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. Gabriel phthalimide synthesis is method of preparation of aliphatic primary amine from phthalimide and alkyl halide. Heat the flask on an oil bathsand bathheating mantle at 5c till the contents melts, froth up and become solid. Phthalic anhydride and ammonium hydroxide pthalic anhydride and urea. Now go to the chemicalsupply and get a pound or so of.
Reduction of alkyl imines and dialkyl iminium salts. Phthalimide is sufficiently acidic to form a potassium salt by treatment with concentrated potassium hydroxide solution. Request pdf preparation of phthalimide by ammoxidation of oxylene and characterization of vcrosio2 catalyst phthalimide, as an important intermediate of organic synthesis, has been. Alkylation of the phthalimide anion gabriel synthesis gabriel devised a method for the preparation of primary amines unaccompanied by impurities of secondary or tertiary amines. Go to the great big building supply house and pick up a couple of gallons of swimming pool chlorination liquid. The complex natural product was also reduced with high stereoselectivity by hydrogenwilkinsons catalyst. The crystal structure of l1 has been solved by direct methods and refined by fullmatrix least squares. Phthalimide reacts with koh to form potassium phthalimide,which further racts with alkyl halide to form alkyl halide to form nalkyl phthalimide. Other syntheses of phthalimideprotected amino groups.
Amines and its preparation methods study material for. The title com pound has been characterized by elemental analysis, ftir, 1h and c nmr techniques. Synthetic of phthalimides via the reaction of phthalic. Reduction and preparation of a phthalimide derivative from. Yanagimoto is heated for a desired time under a desired pressure in the form of powder or of pellet made by compressing the mixed. Procedure about 20 grams of sodium hydroxide from drain cleaner is added to 100 ml of ice water in a 500 ml widemouthed.977 258 1490 1344 1428 759 134 533 1306 469 1575 1033 326 1153 623 1034 651 754 1286 675 789 459 733 1291 209 1169 1196 36 522 1444 1252 197 1442 541 1164 904 1318 549 1436 1450