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Synthesis of Some Aiæides of Gentisio Aoid Dissertation

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Synthesis of Some Aiæides of Gentisio Aoid Dissertation SYNTHESIS OF SOME AIÆIDES OF GENTISIO AOID DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By ALLEN I. DHŒS, B. S., M. Sc, ****** The Ohio State Uhiversity 1958 Approved by: Department of Pharmaoy ACKNOV/LEDaMTS I wish to acknowledge the generous advice and assistance rendered by Dr. Frank V/. Bope, Associate Professor of Pharmacy, in the development of this dissertation. To the American Foundation for Pharmaceutical Education, I wish to express my gratitude for extending to me financial assistance in the form of a Fellowship— without this assistance it would not have been possible for me to complete my graduate studies. To the members of the faculty of the College of Pharmacy of The Ohio State University, I wish to express my sincere appreciation for their guidance throughout my graduate studies, I also wish to eatress my sincere thanks and grate­ ful appreciation to all others who have assisted me in any way. As a final note, I would like to thank my wife, Charlotte, for her wonderful moral support during the com­ pletion of my graduate studies; for behind every man there is his wife. ii TABLE OF CONTENTS Page INTRODUCTION .......... 1 DISCUSSION OF LITERATURE General ........................ 3 Some New Gentisio Aoid Derivatives 15 Preparation of Amides .......... 16 GENERAL PROCEDURES 21 EXPERIMENTAL 23 Preparation of 2,5- Dimethoiybenzoio Acid . , 23 Preparation of 2,5- Dimethoxybenzoyl Chloride 26 Classification of N- Substituted Amides Prepared 27 Monosubstituted Amides of 2,5- Dimethoxybenzoio A o i d ........................................ 29 Alkyl ...................................... 29 N- n- Propyl- 2,5- Dimethoxybenzamide . 29 N- n- Butyl- 2,5- Dimethoxybenzamide . 31 N- Isoamyl- 2,5- Dimethoxybenzamide .... 32 Dialkylaminoalkyl....................... 33 N - y - Dimethylaminopropyl- 2,5- Dimethoxy­ benzamide Hydrochloride ................ 33 N - y - Diethylaminopropyl- 2,5- Dimethoxy­ benzamide Hydrochloride ......... 34 Alicyclio .................................. 36 N- Cyclohexyl- 2,5- Dimethoxybenzamide . , . 36 Aromatic .......... ...... ............ 37 N- 2*- Methylphenyl- 2,5- Dimethoxybenzamide 37 N- 5* - Methylphenyl- 2,5- Dimethoxybenzamide 39 N- 4»- Methylphenyl- 2,5- Dimethoxybenzamide 40 N- 2*,6 * - Dimethylphenyl- 2,5- Dimethoxy­ benzamide ............... » 41 N- 2»,5*- Dimethylphenyl- 2,5- Dimethoxy­ benzamide .............................. 41 N- 2*,4'- Dimethylphenyl- 2,5- Dimethoxy­ benzamide .......... •.................. 42 N- p- Diethylaminophenyl- à,5- Dimethoxy­ benzamide Hydrochloride ................ 43 Aralkyl .................................... 44 N- Benzyl- 2,5- Dimethoxybenzamide........ 44 N- ^ - Phenylethyl- 2,5- Dimethoxybenzamide 46 iii Page Heterooyolio A l k y l ............................ 47 N - y - (4- Morphollno) propyl- 2,5- Dimethoxy­ benzamide Hydroohloride .................. 47 Disubstituted Amides of 2,5- Dimethoxybenzoio Aoid 49 D i a l k y l ...................................... 49 N,N- Diisobutyl- 2,5- Dimethoxybenzamide . 49 N,N- Diisoamyl- 2,5- Dimethoxybenzamide . 51 D i a r a l k y l .................................... 52 N,N- Dibenzyl- 2,5- Dimethoxybenzamide .... 53 Misoellaneous Amides of 2,5- Dimethoxybenzoio Aoid 53 N- (2,5- Dimethoxybenzoy1) pyrrolidine .... 53 N- (2,5- Dimethoxybenzoyl) piperidine .... 55 2,5- DimethoxybenzoylUr e a .................. 56 INFRARED SPECTROSCOPY ............. 59 INFRARED SPECTROGRAPHS MD THEIR INTERPRETATION . 65 OPTICAL PROPERTIES................................. 100 DISTRIBUTION S T U D Y ................................. 102 SUÎMARY AND DISCUSSION............................. 109 CONCLUSIONS....................................... 122 LIST OF REFERENCES................................. 125 AUTOBIOGRAPHY..................................... 130 ±7 LIST OF TABLES Table Page I. Absorption Bands for Known Groups of Atoms as Compiled by The Ohio State University , . 64 II. Absorption Bands Found in 8,5- Dimethozy- benzoio A c i d ........ ................... 68 III. Absorption Bands Found in N- Alkyl Substi­ tuted Amides of 2,5- Dimethoxybenzoio Aoid 73 IV. Absorption Bands Found in N- Dielkylamino- alkyl Substituted Amides of 2,5- Dimethoxy benzoic Aoid .......................... 76 V. Absorption Bands Found in N- Cyclohexyl- 2,5 Dimethoxybenzamide .................... 78 VI. Absorption Bands Found in N- Aromatic Substi tuted Amides of 2,5- Dimethoxybenzoio Acid 86 VII. Absorption Bands Found in N- Aralkyl Substi­ tuted Amides of 2,5- Dimethoxybenzoio Acid 90 VIII. Absorption Bands Found in N- - (4- Morpho- lino) propyl- 2,5- Dimethoxybenzamide . 91 IX. Absorption Bands Found in N- Disubstituted Amides of 2,5- Dimethoxybenzoio Aoid . 97 X. Absorption Bands Found in N- (2,5- Dimethoxy benzoyl) Piperidine and N- (2,5- Dimethoxy benzoyl) Pyrrolidine ................ 98 XI. Absorption Band Found in 2,5- Dimethoxyben­ zoyl urea .......... .......... 98 XII. Alpha and Gamma Refractive Indices of the Crystalline N- Substituted Amides # # # 101 XIII. Distribution Coefficients (K) Obtained with N- y - Dimethylaminopropyl- 2,5- Dimethoxy benzamide .*.... ......... • . • . 105 Table Page TTT, Distribution Coefficients (K) .............. 107 3CV, Summary of Mono substituted Amides of 2,5- Dimethoxybenzoio Aoid P r e p a r e d .......... 117 z n . Summary of N- Disubstituted Amides of 2,5- Dimethoxybenzoio Aoid P r e p a r e d .......... 118 X7TI. Summary of Misoellaneous Amides of 2,5- Dimethozybenzoio Aoid Prepared ...... 118 vi LIST OF FIGURES Figure Page 1. Infrared Spectrograph of 2,5- Dimethoxyhenzoic A o i d ........................................ 68 2. Infrared Spectrograph of N- n- Propyl- 2,5- Dimethoxybenzamide.......................... 70 3. Infrared Spectrograph of N- n- Butyl- 2,5- Dimethoxybenzamide . • ................ 71 4. Infrared Spectrograph of N- Isoamyl- 2,5- Dime thoxyb enzamide..................... 72 5. Infrared Spectrograph of N- y - Dimethylamino­ propyl- 2,5- Dimethoxybenzamide Hydro­ chloride ............................... 74 6 . Infrared Spectrograph of N- y - Diethylamino­ propyl- 2,5- Dimethoxybenzamide Hydro­ ohloride .................................. 75 7. Infrared Spectrograph of N- Cyclohexyl- 2,5- Dimethoxybenzamide........................ 77 8 . Infrared Spectrograph of N- 2»- Methylphenyl- 2.5- Dimethoxybenzamide ........ 79 9. Infrared Spectrograph of N- 3 Methyl phenyl- 8 .5- Dimethoxybenzamide . ........... 80 10. Infrared Spectrograph of H- 4*- Methylphenyl- 2.5- Dimethoxybenzamide............... 81 11. Infrared Spectrograph of N- 2',6 '- Dimethyl­ phenyl- 2,5- Dimethoxybenzamide......... 82 12. Infrared Spectrograph of N- 2*,5*- Dimethyl­ phenyl- 2,5- Dimethoxybenzamide......... 83 13. Infrared Spectrograph of N- 2*,4*- Dimethyl­ phenyl- 2,5- Dimethoxybenzamide.......... 84 Tii Figure Page 14. Infrared Speotrograpli of N-/»- Diethylamino­ phenyl- 2,5- Dimethoiyhenzamide Hydro­ ohloride ................ « ............... 85 15. Infrared Spectrograph of N- Benzyl- 2,5- Dime thoxyb enzamide .......................... 87 16. Infrared Spectrograph of N - ^ - Phenylethyl- 2.5- Dimethoxybenzamide ............ 88 17. Infrared Spectrograph of N- X - (4- Morpho- lino) propyl- 2,5- Dimethoxybenzamide Hydrochloride............................ 89 18. Infrared Spectrograph of N,N- Diisobutyl- 2.5- Dimethoxybenzamide • 92 19. Infrared Spectrograph of N,N- Diisoamyl- 2,5- Dimethozyb enzamide ............... 95 20. Infrared Spectrograph of N,N- Dibenzyl- 2,5- Dimethoxybenzamide .............. 94 21. Infrared Spectrograph of N- (2,5- Dimethoxy­ benzoyl) Piperidine . ................... 95 22. Infrared Spectrograph of N- (2,5- Dimethoxy­ benzoyl) Pyrrolidine ................. 96 23. Infrared Spectrograph of 2,5- Dimethoxybenzoyl u r e a ...................................... 99 24. Plot of the Log of the Distribution Coeffi­ cients (log £) vs. p H ..................... 108 vlli INTRODUCTION Salicylic acid and sodium salicylate have been employed as analgetics for many years. In the body, salicylic acid is biologically oridized to gentisic aoid. Gentisic acid (2,5- dihydroiybenzoio acid) has also been shown to possess analgetic and antipyretic properties (1, 2, 3, 4). Salicylamide is also used as an analgetic and anti­ pyretic, and in more recent years gentisic aoid amide has been shown to possess analgetic and antipyretic properties similar to salicylamide and salicylic acid (5, 6 , 7). The relationship among these compounds can be seen from the following structural formulae: HO- 7 \ \ c ' OH 7 \\/oH salicylic acid gentisic aoid NHi salioylamlde gentisamide 2 Since both salicylic acid bûA gentisic acid as well as their simple amides possess analgetic properties, this investigation was directed toward the preparation and study of some derivatives of gentisic acid in the fozm of N- substituted amides. By using different amines that have been shown to possess analgetic or depressant action either alone or in chemical combination with other compounds that do possess such activity, it is hoped that some new important compounds can be added to the presently available analgetics. DISCUSSION OP THE LITERATURE General Although salicylic acid has been used for the treatment of rheumatic conditions since 1376 and sodium salicylate since 1877, gentisic acid, the biological oxidation product of salicylic acid (8 ), was not used medicinally until 1948, In that year Meyer and Ragen (1) salicylic acid gentisic acid
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