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Chapter – 4 Studies on different types of reactions….. content of the flask was poured on crushed ice to isolate the product. The separated product was filtered off and it was washed with cold water to remove acidity. It was dried at 65°C and recrystallized from the mixture of DMF-Methanol to give crystalline pyrazole aldehyde in good yield. Code No. MF MW (g/m) MP (°C) % Yield PA-01 C16H11N3O3 293 162-164 75 PA-02 C16H11N3O3 293 176-178 70 PA-03 C16H12N2O 248 144-146 68 PA-04 C16H11ClN2O 282 142-144 71 PA-05 C16H11FN2O 266 148-150 70 4.9.2 PREPARATION OF 3-ACETYL-4-HYDROXYCOUMARIN STEP – 1 PREPARATION OF 4-HYDROXYCOUMARIN It was prepared according to the method reported by Shah et. al. d Yield - 55 %, MP - 210-212°C. (210-212°C b ) STEP – 2 PREPARATION OF 3-ACETYL-4-HYDROXYCOUMARIN It was prepared according to the method reported by Dholakia et. al. e Yield - 60 %, MP - 120-122°C. (121-122°C c ) 4.9.3 PREPARATION OF 1-(2, 6-DICHLOROPHENYL)-2-INDOLINONE It was prepared according to the literature method. f, g, h, i Yield - 60 %, MP - 126-128°C. (124°C-126°C e ) d A. K. Shah, N. S. Bhatt and V. M. Thakor; Curr. Sci., 1984, 53(24), 1289. e V N. Dholakia, M. G. Parekh and K. N. Trivedi; Aust. J. Chem., 1968, 21, 2345. f G. S. Predvoditeleva, T. V. Kartseva, O. N. Oleshko, V. I. Shvedov, R. D. Syubaev, G. Ya. Shvarts, L. M. Alekseeva, O. S. Shvedov, V. V. Chistyakov and Yu. N. Sheinker; Khim.-Farm. Zh., 1987, 21, 441. g P. Moser, A. Sallmann and I. Wiesenberg; J. Med. Chem., 1990, 33, 2358. h A. Sallmann and R. Pfister; British Patatent 1,132,318, 1968. (CA 70:57455b) i A. Sallmann and R. Pfister; Ger. Offen. 1,815,802, 1969. (CA 72:12385d) Department of Chemistry, Saurashtra University, Rajkot – 360 005 225
Chapter – 4 Studies on different types of reactions….. 4.9.4 GENERAL PROCEDURE FOR THE PREPARATION OF DNJ-701 TO DNJ-705 METHOD – (A) CONVENTIONAL APPROACH 0.01 mole of 1-(2, 6-dichlorophenyl)-2-indolinone was dissolved into 30 ml of methanol into 100 ml round bottom flask. 0.01 mole of an appropriately substituted pyrazole-4-carboxaldehyde was added to the above flask along with catalytic amount of piperidine. The reaction mixture was refluxed on water bath for 5-7 hours. The progress and the completion of the reaction were checked by silica gel-G F254 thin layer chromatography using hexane : ethyl acetate (6 : 4) as a mobile phase. After the reaction to be completed, the reaction mixture was cooled to room temperature and the product was separated by filtration. The product was washed with methanol and dried to give desired product in moderate yield which was recrystallized by DMF. (Physical data of the synthesized end products are summarized in the table 4.10.1) METHOD – (B) MICROWAVE APPROACH 0.01 mole of 1-(2, 6-dichlorophenyl)-2-indolinone was dissolved into 20 ml of dimethylformamide into 100 ml microwave flask. 0.01 mole of an appropriately substituted pyrazole-4-carboxaldehyde was added to the above flask along with catalytic amount of piperidine. The reaction mixture was irradiated under microwave irradiation using Qpro-M microwave synthesizer for the desired time at 400 W. The progress and the completion of the reaction were checked at the interval of every one min. by silica gel-G F254 thin layer chromatography using hexane : ethyl acetate (6 : 4) as a mobile phase. After the reaction to be completed, the reaction mixture was cooled and scratched into 30 ml of methanol. The separated product was filtered off and washed with methanol and it was dried to give desired product in good yield which was recrystallized by DMF. (Physical data of the synthesized end products are summarized in the table 4.10.1) Department of Chemistry, Saurashtra University, Rajkot – 360 005 226
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Saurashtra University Re - Accredit
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Statement under O. Ph. D. 7 of Saur
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ACKNOWLEDGEMENT It is a moment of g
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Jignesh Lunagariya, Hitesh Sarvaiya
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CONTENT Content General Remarks 6 A
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Content 3.2 Reaction scheme 149 3.3
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5.14 Conclusion 313 5.15 Spectral r
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MF Molecular Formula MW Molecular W
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GABA Gamma Amino Butyric Acid MES M
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PART - A STUDIES ON 2-METHYL INDOLI
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Part-A Studies on 2-methyl indoline
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CHAPTER - 1 PREPARATION AND YIELD O
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Chapter - 1 Preparation and Yield o
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Chapter - 2 Microwave assisted simp
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Part - B Studies on isatin derivati
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CHAPTER - 3 PREPARATION OF SMALL LI
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Chapter - 3 Preparation of small li
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Chapter - 5 Synthesis and Character
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Chapter - 6 Biological evaluation o
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Summary Synthesis and biological pr
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Summary Synthesis and biological pr
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Conferences / Seminar / Workshop At
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