Isatin → HCID 178448701, compound

HRID 1876256Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[C:12]([NH:20][NH2:21])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:2]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:4](=[N:21]/[NH:20][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)/[C:2]1=[O:3])[CH2:4][CH2:6][CH3:7]

Participants

Reactant 2

HCID 7054Isatin

HCID 11955Benzoylhydrazine

Product 1

HCID 178448701HCID 178448701, compoundYield 65.3%

Procedure

The title compound was prepared as a yellow solid, using isatin 5 and benzhydrazide according to the synthetic method D. The resulting solid was washed with ethanol. Yield: 65.3%. 1H NMR (DMSO-d6): δ 0.95 (t, J=7.5 Hz, 3H), 1.36-1.41 (m, 2H), 1.64-1.69 (m, 2H), 3.78 (t, J=7.2 Hz, 2H), 7.19 (t, Hz, J=7.5 Hz, 1H), 7.24 (d, J=7.8 Hz, 1H), 7.49 (td, J=1.2 Hz, J=7.8 Hz, 1H), 7.60-7.73 (m, 4H), 7.90-7.92 (m, 2H), 13.90 (br, s 1H). 13C NMR (DMSO-d6): δ 14.06 (CH3), 20.04 (CH2), 29.56 (CH2), 39.49 (CH2), 110.69 (CH), 119.66 (C), 121.26 (CH), 123.69 (CH), 127.88 (CH), 129.67 (CH), 132.22 (CH), 132.43 (C), 133.40 (CH), 137.40 (C), 143.43 (C═N), 161.58 (C═O), 163.34 (C═O). HRMS (ES+) calcd for C19H20N3O2 (M+H+), m/e, 322.1548; found, 322.1550.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-9951c0ee73714dc483e12d30335b32f6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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