INTRODUCTION:

Pyrazolinones are oxo derivatives of pyrazoline. Pyrazolinone were effective anti-oxidant ¹ for rubber and linseed oil and responsible for inhibition of odor formation in synthetic detergent². They possess wide range of pharmacological activities as bacteriostatic³, bactericidal^{4, 5}, fungicidal^{6, 7}, anti-pyretic^{8, 9}, analgesic¹⁰, anticoagulant¹¹, anti-anthelmintic¹², anti-rheumatic^{13, 14}, germicidal¹⁵, etc.

4- (R) phenyl hydrazono- N’-4-butyl amino malonyl –3- methyl -2-pyrazolin-5-one.

Where, R= 2-CH₃, 2-OC₂H_5,4- NO₂, 4-Cl, 4-CH₃, 3, 4 (CH₃)₂; R’= -CH₂-CH₂- CH₂-CH₃

MATERIAL AND METHOD:

All reagents and solvents were procured from Sigma Aldrich. Melting Points were determined in open capillaries on Electro-thermal apparatus and were uncorrected. Infrared (IR) spectra were recorded on Perkin Elmer RX-1 using KBr wafers.

General procedure for the synthesis of N (4-butyl) phenyl malonamic acid hydrzide:

3 ml of 4-butyl aniline and 6ml of diethylmalonate was refluxed for 1 hr. When dianillide get separated, filtrate was collected in china dish and concentrated by heating on boiling water bath. White sticky mass of ethyl –N-(4 butyl) malonamate was obtained and finally treated with petroleum ether. 2.6 gm of ethyl -N--(4 butyl) phenyl malonamate in 20 ml of ethanol was treated with 4 ml of hydrazine hydrate (98 %), white crystalline compound was obtained which was recrystallized from hot ethanol.

Synthesis of ethyl-2, 3 –dioxo butyrate -2- (substituted) phenyl hydrazone:

3 ml of substituted aniline was diazotized by adding conc. HCl (6 ml) and diluted with 6 ml distilled water and cooled to 0ºc. 10 ml NaNO₂solution was added with constant stirring. Finally mixture of sodium acetate (1.5 gm) and ethylacetoacetate (2 ml) in 10 ml of ethanol was added. The solid which separated was filtered, washed with cold water and recrystallized with dilute ethanol.

TABLE – I Pyrazolinones obtained by the condensation of ethyl 2-3, di –oxo butyrate 2- (R) phenyl hydrazone with N-(4 -butyl) phenyl malonamic acid hydrazide

S.N	R	Mol. Formula	M.PºC	Yield %	Nitrogen % Found Cal		Carbon % Found Cal		Hydrogen % Found Cal		I.R v cm^-1
1	2-Cl	C₂₃H₂₄O₂N₅Cl	171	48.05	15.62	15.43	60.89	60.85	5.19	5.29	3280 cm^-1(NH), 1649cm^-1 (C=O), 1576 cm^-1 (>C=N), 1541 cm^-1 (N-N), 1349 cm^-1 (-CH₃ bonding), 1249 cm^-1 (-C-N )
2	4- Cl	C₂₃H₂₄O₂N₅Cl	189	45.76	15.48	15.43	60.88	60.85	5.21	5.29	3284 cm^-1(NH), 1654 cm^-1 (C=O), 1565 cm^-1 (>C=N), 1531 cm^-1 (N-N), 1335 cm^-1 (-CH₃ bonding), 1256 cm^-1 (-C-N )
3	2-CH₃	C₂₄H₂₇O₂N₅	193	50.35	16.25	16.16	66.56	66.50	6.29	6.23	3290 cm^-1(NH), 1660 cm^-1 (C=O), 1592 cm^-1 (>C=N), 1546 cm^-1 (N-N), 1350 cm^-1 (-CH₃ bonding), 1260 cm^-1 (-C-N )
4	4-CH₃	C₂₄H₂₇O₃N₅	180	43.16	16.27	16.16	66.58	66.5	6.25	6.23	3296 cm^-1(NH), 1665 cm^-1 (C=O), 1595 cm^-1 (>C=N), 1550 cm^-1 (N-N), 1358 cm^-1 (-CH₃ bonding), 1269 cm^-1 (-C-N )
5	2-OC₂H₅	C₂₄H₂₉O₄N₅	171	44.84	15.59	15.52	63.85	63.80	6.49	6.43	3286 cm^-1(NH), 1687cm^-1 (C=O), 1596 cm^-1 (>C=N), 1566 cm^-1 (N-N), 1359 cm^-1 (-CH₃ bonding), 1250 cm^-1 (-C-N )
6	3,4-(CH₃)	C₂₅H₂₉O₃N₅	200	46.51	15.72	15.65	67.17	67.11	6.53	6.48	3291 cm^-1(NH), 1673 cm^-1 (C=O), 1584 cm^-1 (>C=N), 1557 cm^-1 (N-N), 1348 cm^-1 (-CH₃ bonding), 1279 cm^-1 (-C-N )
7	4-NO₂	C₂₃H₂₄O₅N₆	199	40.26	18.15	18.10	59.52	59.48	5.17	5.07	3287 cm^-1(NH), 1660 cm^-1 (C=O), 1592 cm^-1 (>C=N), 1568 cm^-1 (N-N), 1340 cm^-1 (-CH₃ bonding), 1272 cm^-1 (-C-N )

TABLE- II Antibacterial activity screening of some of the compounds

S.N

Name of the compound

Concentration

In H gm/ml

Sensitivity

Pseudomonas

Stapphylococcus

E.coli

B.subtilis

4- (4- chloro) phenyl hydrazono- N’-4-Butyl amino malonyl –3- methyl -2-pyrazolin-5-one.

4- ( 4- nitro) phenyl hydrazono- N’-4-Butyl amino malonyl –3- methyl -2-pyrazolin-5-one.

4- (4- methyl) phenyl hydrazono- N’-4-Butyl amino malonyl –3- methyl -2-pyrazolin-5-one.

4- (3, 4-dimethyl) phenyl hydrazono- N’-4-Butyl amino malonyl –3- methyl -2-pyrazolin-5-one

Synthesis of 4- (substituted) phenyl hydrazono- N’-4-Butyl amino malonyl –3- methyl -2-pyrazolin-5-one.

0.26 gm of ethyl-2, 3 –dioxo butyrate -2- (substituted) phenyl hydrazone (1 mol) and 0.24 gm N (4-butyl) phenyl malonamic acid hydrazide dissolved in 10 ml of ethanol was refluxed for 2 hrs using glacial acetic acid as catalyst and finally recrystallized from ethanol and purity has been checked by TLC using silica gel G plates in 10 % methanol/benzene.

RESULTS AND DISCUSSION:

The results of m. p. %Yield , %Nitrogen, %Carbon, % Hydrogen were discuss in table no. 1 and Antibacterial activity screening of some of the compounds was discuss in table 2.

ACKNOWLEDGEMENT:

The authors thank the authorities of the CDRI, Lucknow for spectral and analytical data

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