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Chapter – 3 Preparation of small library…..
atmosphere, four protons of methylene groups flipped individually and
peaks got merged.
3. Four protons of two morpholinyl methylene groups (C2 & C6) gave
quintet at 3.69 δ ppm.
4. Two protons of methylene group (C7) attached to two nitrogen atoms of
indolinone and morpholine ring gave singlet at 4.48 δ ppm.
5. There are four aromatic protons in the molecule. One proton of C13
gave quintet (triplet-doublet) at 7.15 δ ppm. One proton of C15 gave
quartet at 7.39 δ ppm while one proton of C14 gave doublet at 7.62 δ
ppm. Rest of the proton of C16 gave doublet at 7.80 δ ppm.
6. One most deshielded proton of secondary amine in hydrazide linkage
(-NH) gave singlet in the down field at 12.52 δ ppm.
13 C NMR spectral interpretation of N'-[1-(morpholin-4-ylmethyl)-2-oxo-1,
2-dihydro-3H-indol-3-ylidene]-2-propylpentanohydrazide (DNJ-1301)
1. Two most shielded methyl carbons of n-propyl chain (C25 & C28)
showed peak at 14.07 δ ppm.
2. Two methylene carbons of n-propyl chain (C24 & C27) showed peak at
20.68 δ ppm.
3. Another two methylene carbons (C23 & C26) showed peak at 34.58 δ
ppm.
4. Methine carbon of hydrazide linkage (C22) showed peak at 51.00 δ
ppm.
5. Two methylene carbons (C3 & C5) of morpholinyl ring gave peak at
51.94 δ ppm. While another two methylene carbons of morpholinyl ring
(C2 & C6) showed peak at 66.92 δ ppm.
6. Methylene carbon (C7) attached to both the nitrogen of indole nucleus
and morpholine nucleus gave peak at 66.59 δ ppm.
7. Peaks obtained at 76.89, 77.21, 77.53 δ ppm are due to the solvent
CDCl3.
8. Peaks obtained at 110.44, 119.53, 119.95, 120.33, 136.04 and 143.19
δ ppm are due to the aromatic carbons C13, C15, C16, C11, C14 and C12
respectively.
Department of Chemistry, Saurashtra University, Rajkot – 360 005 168