Isatin → HCID 178444727, compound

HRID 1876250Notes

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].[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([NH:19][NH2:20])=[O:18])=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([NH:19]/[N:20]=[C:4]2\[C:2](=[O:3])[N:1]([CH2:2][CH2:4][CH2:6][CH2:7][CH2:8][CH3:9])[C:11]3[C:6]\2=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:18])=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 7054Isatin

HCID 108164-Chlorobenzohydrazide

Product 1

HCID 178444727HCID 178444727, compoundYield 80%

Procedure

The title compound was prepared as a yellow solid, using isatin 3 and 4-chlorobenzhydrazide according to the synthetic method E. The resulting solid was washed with ethanol. Yield: 80%. 1H NMR (DMSO-d6): δ 0.85 (t, J=6.9 Hz, 3H), 1.25-1.38 (m, 6H), 1.64 (m, 2H), 3.76 (t, J=7.2 Hz, 2H), 7.18 (t, J=7.8 Hz, 1H), 7.23 (d, J=7.8 Hz, 1H), 7.48 (t, J=7.8 Hz, 1H), 7.64-7.72 (m, 3H), 7.91-7.94 (m, 2H), 13.85 (br s, 1H). 13C NMR (DMSO-d6): δ 14.32 (CH3), 22.41 (CH2), 26.37 (CH2), 27.38 (CH2), 31.31 (CH2), 39.80 (CH2), 110.69 (CH), 119.56 (C), 121.33 (CH), 123.72 (CH), 129.75 (CH), 131.20 (C), 132.35 (CH), 138.23 (C), 143.52 (C═N), 161.55 (C═O). HRMS (ES+) calcd for C21H23N3O2Cl (M+H+), m/e, 384.1484; found, 384.1473.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-0e1d581c4da1444bbf03689a99cd60a3
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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