Chemistry Learner Salt about chemistry Inorganic Chemistry Chemical Bones ‘Chemis Reseeons Materials Chemistry Organic Chemistry Petodi Table Perodie Trends Period Table Groups How to Rese Period Table Worksheets [Naming Covalent Compounds Worksheets [Netlonic Equation Worksheets Types of Chemical Reactions Worksheets ‘Word Equations Worksheet: Valence Electrons Workenets Periodic Trends Worksheets ‘Graphing Periodic Trends Worksheats Periodic Trandslorszaton Energy Worksheats ‘tome Structure Worksheets ‘Atomic Structure Ard Isotopes Worksheets Home 0 Glass-lined Reactors clase he Chemistry / Fischer Indole Synthesis. Fischer Indole Synthesis 8) Defi ‘TABLE OF CONTENTS What is Definition: What is Fischer Fischer [hen Indole eon Synthesis? sirsenairane The Fiseher indole symthesisis an organic reaction used to convert a phenythyarazine and an aldehyde lr ketone to an indole using an acid catalyst like Bronsted or Lewis acids. An application of this reaction isthe synthesis of antimigraine ‘TRENDING ToPICcs pl scale Diatomic Molecules |s Frying an Egg a Chemical Change? 's Dissolving a Chemical Change? | Baking a Cake Physical or Chemical Change? |e Bolling Wat Chemical Change? Solvation Dihydroxylation Heat of Solution eal FluidFischer Indole Synthesis Phenylhydrazine Ketone Acid R 1 ens + NH, + H,O — I H Indole Ammonia Water Fischer Indole Synthesis ‘The history ofthis reaction goes back to 1883 when the reaction was first discovered by a German, chemist Emi Fischer. Examples of Fischer Indole Synthesis The Fisher indole synthesis is used to synthesize 2-phenylindole and tetrahydrocarbazote 259) ox Glass-lined ReactorsFischer Indole Synthesis Examples N F i i - NH, H Phenylhydrazine Acetophenone 2-Phenylindole ° © C) CG NH. +t . CY nn? -H,0 1 i -NH, H Phenylhydrazine Cyclohexanone 1,2,3,4-tetrahydrocarbazole Fischer Indole Synthesis Examples 2 Phenylindole Tetrahydracarbazole Mechanism of Fischer Indole Synthesis Phenylhydrazone i fred from a condensation reaction of phenylhydrazine and an aldehyde of ketone, The phenythyarazone converts into an indole inthe presence ofan acid catalyst 28401 Mechanism of Fischer Indole Synthesi Step 1: Condensation reaction between an arylhydrazine and an aldehyde or ketone rroducing an arylhydrazone R, Cy a 2 OR i 7 H,0 Nv H Phenylhydrazine Ketone Phenylhydrazone Step 2: Rearrangement of the arylhydrazone to an enamine R oR of — Op Step 3: Rearrangement of the enamine form a new C-C bond though 3.3-sigmatropic shift forming a diimine R, eee , wi i Step 4: Final rearrangement restores the benzene ring and simultaneously clases the five member ring, The douiole bond in the five member ring is formed with the loss of ammonia to give the final indole product. 4 HE op, > AR we R en « x — Orpee 2 Crp. Yu 4 ~ NH, 1 4 IndoleFischer Indole Synthesis Mechanism References: 1. Definition - Chemtubesd.com Definition, example, and mechanism ~ Pubsacs.org Definition, example, and mechanism ~ Rezearchgatenet 4: Definition and mechanism ~ Na ‘5. Definition and mechanism ~ Organic-chemistry.ors 6 Definition and mechanism ~ Ch.ic.ack 7. Definition and mechanism ~ Synarchive Definition and mechanism ~ Onlinebrary.witey.com Example ~ Sslancedivect.com 8 Mechanism ~ Nature.com 4M Mechanism — Users.mlamioh.edu Glass-lined Reactors ox Glass-lined Reactors Related ArticlesAlkyne Dihydroxylation Methylation zene Ring Reactions Reactions Leave a Reply ‘Your email adcross wil not be published, Required fds are matkod * Comment * Website About Contact ©7025 Chemisty Lean