Supplementary Details

Supplementary Details

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl) methylene] benzohydrazide (4a)

IR: vmax (cm-1):3267 (NH),1658(C=O), 1608(C=N)

1H NMR(CDCl3) (δ,ppm): 9.4(s,1H, NH, D2O exchangeable), 8.37(s,1H, CH=N), 7.82-7.43 (m,10H, Ar-H), 2.39(s, 3H, CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-4-methylbenzohydrazide(4b)

IR: vmax (cm-1):3270 (NH),1645 (C=O), 1619 (C=N)

1H NMR(CDCl3) (δ,ppm): 9.26(s,1H, NH), 8.38 (s, 1H, CH=N), 7.78-7.24 (m, 9H, Ar-H), 2.60(s, 3H, Ar-CH3), 2.41(s, 3H, CH3)

Mass spectra: M+ (353), M-1 (352), M+2 (355)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-4-nitrobenzohydrazide(4c)

IR: vmax (cm-1): 3259 (NH), 1647 (C=O), 1605 (C=N)

1H NMR(CDCl3) (δ,ppm): 9.41(s, 1H, NH), 8.43 (s, 1H, CH=N), 8.34 (d, 2H, 3’,5’ Ar-H), 8.21 (d, 2H, 2’,6’ Ar-H), 7.78-7.75(d, 2H, Ar-H), 7.58-7.53 (t, 2H, Ar-H),7.42-7.37 (t, 1H, Ar-H), 2.39(s, 3H, CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]isonicotinohydrazide(4d)

IR: vmax (cm-1):3261 (NH), 1666 (C=O), 1602 (C=N)

1H NMR(CDCl3) (δ,ppm): 9.31(s, 1H, NH), 8.96(d, 2H, 2’,6’INH), 8.43(s, 1H, CH=N), 8.01(d, 2H, 3’,5’INH), 7.78-7.75(d, 2H, Ar-H), 7.58-7.53(t, 2H, Ar-H), 7.42-7.37 (t, 1H, Ar-H), 2.41(s, 3H, CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-2-(4-chlorophenyl)acetohydrazide(4e)

IR: vmax (cm-1): 3273 (NH),1665 (C=O), 1611 (C=N)

1H NMR(CDCl3) (δ, ppm): 9.40(s,1H, NH), 8.66 (s, 1H, CH=N), 7.56-7.34(m, 5H, Ar-H), 7.22-7.14(m, 4H, Ar-H), 3.44 (s, 2H, CH2), 2.53(s, 3H, CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-2-(1-naphthyl)acetohydrazide(4f)

IR: vmax (cm-1): 3201(NH), 1659(C=O), 1613 (C=N)

1H NMR(CDCl3) (δ,ppm): 9.28(s, 1H, NH), 8.3 (s, 1H, CH=N), 7.9-7.3 (m, 12H, Ar-H), 4.11(s, 2H, CH2), 2.37(s, 3H, CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-4-methoxybenzohydrazide (4g)

IR: vmax (cm-1): 3263 (NH), 1662(C=O), 1611(C=N) ;

1H NMR(CDCl3) (δ,ppm): 9.34(s, 1H, NH), 8.39 (s, 1H, CH=N), 7.81-6.95 (m, 9H, Ar-H), 3.81(s, 3H, OCH3), 2.43(s, 3H, CH3)

4-chloro-N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]benzohydrazide(4h)

IR: vmax (cm-1): 3259 (NH), 1648 (C=O), 1612 (C=N) ;

1H NMR(CDCl3) (δ,ppm): 9.39(s, 1H, NH), 8.38 (s, 1H, CH=N), 7.93-7.43 (m, 9H, Ar-H), 2.44(s, 3H, CH3)

2-chloro-N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]benzohydrazide(4i)

IR: vmax (cm-1):3261 (NH), 1642(C=O), 1613(C=N) ;

1H NMR(CDCl3) (δ,ppm): 9.42(s, 1H, NH), 8.38 (s, 1H, CH=N), 7.81-7.32 (m, 9H, Ar-H), 2.43(s, 3H, CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-4-fluorobenzohydrazide(4j)

IR: vmax (cm-1): 3266 (NH), 1645(C=O), 1610(C=N) ;

1H NMR(CDCl3) (δ,ppm): 9.48(s, 1H, NH), 8.36(s, 1H, CH=N), 8.05(d, 2H, 3’,5’ Ar-H), 7.82-7.21 (m,7H, Ar-H), 2.44(s, 3H, CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-2-phenoxyacetohydrazide(4k)

IR: vmax (cm-1): 3240 (NH), 1652 (C=O), 1613 (C=N) ;

1H NMR(CDCl3) (δ,ppm): 9.39(s, 1H, NH), 8.29 (s, 1H, CH=N), 7.81-6.82(m, 10H, Ar-H), 5.17(s, 2H, CH2), 2.45(s, 3H, CH3)

2-(4-Isobutyl- phenyl)-propionic acid(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl methylene)-hydrazide(4l)

IR: vmax (cm-1):3255 (NH), 1707(C=O), 1625(C=N) ;

1H NMR(CDCl3) (δ,ppm): 9.27(s, 1H, NH), 8.28 (s, 1H, CH=N), 7.82-7.33(m, 9H, Ar-H), 3.98 (q, 1H, -CH(methyl)-), 2.53 (d, 2H, -CH2-), 2.37 (s, 3H, CH3), 2.22 (m, 1H, CH), 1.65 (d, 3H, CH3), 1.16 (d, 6H, 2 X CH3)

N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-2-phenylacetohydrazide(4m)

IR: vmax (cm-1) ; 3268 (NH), 1640 (C=O), 1611 (C=N)

1H NMR(CDCl3) (δ,ppm): 9.36(s, 1H, NH), 8.38 (s, 1H, CH=N), 7.62-7.14(m, 10H, Ar-H), 3.44 (s, 2H, CH2), 2.37 (s, 3H, CH3)

4-bromo-N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]benzohydrazide(4n)

IR: vmax (cm-1): 3269 (NH), 1648 (C=O), 1612(C=N) ;

1H NMR(CDCl3) (δ,ppm): 9.40(s, 1H, NH), 8.34 (s, 1H, CH=N), 7.89 (d, 2H, 2’,6’Ar-H), 7.82-7.79(d, 2H, Ar-H), 7.63-7.54(m, 4H, Ar-H), 7.44-7.38 (t, 1H, Ar-H), 2.43(s, 3H, CH3)

Mass spectra: M+ (417), M-1 (416), M + 2 (419), M + 4 (421)

2,4-dichloro-N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]benzohydrazide (4o)

IR: vmax (cm-1): 3273 (NH), 1649(C=O), 1614(C=N) ;

1H NMR(CDCl3) (δ, ppm): 9.28(s, 1H, NH), 8.37 (s, 1H, CH=N), 7.85-7.33 (m, 8H, Ar-H), 2.43(s, 3H, CH3)