Isatin → HCID 178444723, compound

HRID 1522972Notes

Reaction equation

HRID 1522972 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]1([C:22]([NH:24][NH2:25])=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>>[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:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[O:23])/[C:2]1=[O:3])[CH2:4][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 7054IsatinHCID 726891-Naphthohydrazide

Product 1

HCID 178444723HCID 178444723, compoundYield 58%

Procedure

The title compound was prepared using isatin 3 and 1-naphthhydrazide according to the synthetic method E. The product was purified by flash chromatography (eluent: AcOEt/Heptane:3/7) to afford a yellow oil which crystallized. Yield: 58%. 1H NMR (DMSO-d6): δ 0.83 (t, J=6.9 Hz, 3H), 1.26 (m, 6H), 1.59-1.62 (m, 2H), 3.73 (t, J=6.9 Hz, 2H), 7.17-7.23 (m, 2H), 7.48 (t, J=7.2 Hz, 1H), 7.63-7.70 (m, 3H), 7.90 (d, J=6.6 Hz, 1H), 8.07 (t, J=6.6 Hz, 1H), 8.19 (d, J=8.7 Hz, 1H), 8.35 (br s, 1H), 13.51 (br s, 1H). 13C NMR (DMSO-d6): δ 14.29 (CH3), 22.39 (CH2), 26.32 (CH2), 27.34 (CH2), 31.27 (CH2), 39.50 (CH2), 110.61 (CH), 119.61 (C), 121.22 (C), 123.65 (CH), 125.36 (CH), 125.51 (CH), 126.83 (CH), 127.20 (CH), 128.03 (CH), 129.04 (CH), 130.34 (C), 131.26 (C), 132.26 (CH), 133.82 (C), 143.49 (C═N), 161.34 (C═O). HRMS (ES+) calcd for C25H26N3O2 (M+H+), m/e, 400.2033. found, 400.2020.

Workup

  1. customThe product was purified by flash chromatography (eluent: AcOEt/Heptane:3/7)
  2. customto afford a yellow oil which
  3. customcrystallized

Sources & evidence

ORD record
ord-e74830270a70407b8b289684408bae8b
Source dataset
uspto-grants-2015_07
Patent number
US09079854B2

Reaction notes

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