Isatin → HCID 178523949, compound

HRID 1876259Notes

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

Participants

Reactant 2

HCID 7054Isatin

HCID 11955Benzoylhydrazine

Product 1

HCID 178523949HCID 178523949, compoundYield 71.4%

Procedure

The title compound was prepared as a yellow solid, using isatin 7 and benzhydrazide according to the synthetic method D. The resulting solid was washed with ethanol. Yield: 71.4%. 1H NMR (DMSO-d6): δ 1.05-1.09 (m, 2H), 1.18-1.20 (m, 3H), 1.61-1.79 (m, 6H), 3.65 (d, J=7.5 Hz, 2H), 7.22 (t, J=8 Hz, 1H), 7.28 (d, J=8 Hz, 1H), 7.52 (t, J=7.5 Hz, 1H), 7.66-7.70 (m, 3H), 7.75 (t, J=7 Hz, 1H), 7.96 (d, J=7 Hz, 2H), 13.97 (br s, 1H). 13C NMR (DMSO-d6): δ 25.68 (CH2), 26.26 (CH2), 30.71 (CH2), 36.40 (CH), 45.90 (CH2), 110.95 (CH), 119.57 (C), 121.19 (CH), 123.67 (CH), 127.87 (CH), 129.68 (CH), 132.19 (CH), 132.44 (C), 133.40 (CH), 137.70 (C), 143.94 (C═N), 161.90 (C═O), 163.42 (C═O). HRMS (ES+) calcd for C22H24N3O2 (M+H+), m/e, 362.1872; found, 362.1863.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-8a1d3c410ea648698e5d4566ee7a35a8
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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