Isatin → HCID 178446187, compound

HRID 1876257Notes

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][CH2:7][CH3:8]

Participants

Reactant 2

HCID 7054Isatin

HCID 11955Benzoylhydrazine

Product 1

HCID 178446187HCID 178446187, compoundYield 78.1%

Procedure

The title compound was prepared as a yellow solid, using isatin 6 and benzhydrazide according to the synthetic method D. The resulting solid was washed with ethanol. Yield: 78.1%. 1H NMR (DMSO-d6): δ 0.90 (t, J=6.5 Hz, 3H), 1.34-1.36 (m, 4H), 1.63-1.68 (m, 2H), 3.80 (t, J=7 Hz, 2H), 7.22 (t, Hz, J=7.5 Hz, 1H), 7.26 (d, J=7.5 Hz, 1H), 7.52 (t, J=7.5 Hz, 1H), 7.65-7.70 (m, 3H), 7.74 (t, Hz, J=7 Hz, 1H), 7.96 (d, (d, J=7, 2H), 13.95 (br s, 1H). 13C NMR (DMSO-d6): δ 14.30 (CH3), 22.27 (CH2), 27.15 (CH2), 28.89 (CH2), 39.75 (CH2), 110.66 (CH), 119.65 (C), 121.26 (CH), 123.69 (CH), 127.88 (CH), 129.67 (CH), 132.23 (CH), 132.42 (C), 133.40 (CH), 137.80 (C), 143.43 (C═N), 161.58 (C═O), 163.36 (C═O). HRMS (ES+) calcd for C20H22N3O2 (M+H+) m/e, 336.1713; found 336.1707.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-9ed18cdb48f04970b881212a071a0191
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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