Isatin → HCID 178444722, compound

HRID 1522969Notes

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].[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[C:22]([NH:24][NH2:25])=[O:23]>>[CH2:2]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:4](=[N:25]/[NH:24][C:22]([C:13]2[CH:14]=[CH:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)=[O:23])/[C:2]1=[O:3])[CH2:4][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 2

HCID 7054Isatin

HCID 1234852-Naphthohydrazide

Product 1

HCID 178444722HCID 178444722, compoundYield 86%

Procedure

The title compound was prepared as a yellow solid, using isatin 3 and 2-naphthhydrazide according to the synthetic method E. The resulting solid was washed with ethanol. Yield: 86%. 1H NMR (DMSO-d6): δ 0.85 (t, J=6.9 Hz, 3H), 1.22-1.38 (m, 6H), 1.66 (m, 2H), 3.79 (t, J=7.2 Hz, 2H), 7.19 (t, J=7.5 Hz, 1H), 7.24 (d, J=7.8 Hz, 1H), 7.49 (t, J=7.8 Hz, 1H), 7.63-7.73 (m, 3H), 7.94 (dd, J=1.8 Hz, J=8.4 Hz, 1H), 8.05 (d, J=7.5 Hz, 1H), 8.13-8.17 (m, 2H), 8.55, (s, 1H), 14.01 (br s, 1H). 13C NMR (DMSO-d6): δ 14.32 (CH3), 22.44 (CH2), 26.39 (CH2), 27.43 (CH2), 31.33 (CH2), 39.79 (CH2), 110.66 (CH), 119.69 (C), 121.27 (CH), 123.68 (CH), 127.74 (CH), 128.24 (CH), 129.03 (CH), 129.38 (CH), 129.70 (CH), 129.74 (C), 132.21 (CH), 132.63 (C), 135.22 (C), 143.45 (C═N), 161.58 (C═O). HRMS (ES+) calcd for C25H26N3O2 (M+H+), m/e, 400.2031. found, 400.2020.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-9077de32ed024ebaa9f4f55647f03e12
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079854B2

Reaction notes

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