Isatin → HCID 178444729, compound

HRID 1876249Notes

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

Participants

Reactant 2

HCID 7054Isatin

HCID 240032heptanohydrazide

Product 1

HCID 178444729HCID 178444729, compoundYield 32%

Procedure

The title compound was prepared as a yellow solid, using isatin 3 and hexanecarbohydrazide according to the synthetic method E. The resulting solid was washed with ethanol. Yield: 32%. 1H NMR (DMSO-d6): δ 0.82-0.91 (m, 6H), 1.27-1.33 (m, 10H), 1.62 (m, 4H), 2.71 (br s, 1H), 3.74 (t, J=7.2 Hz, 2H), 7.15 (t, J=7.5 Hz, 1H), 7.19 (d, J=7.8 Hz, 1H), 7.45 (t, J=7.8 Hz, 1H), 7.58 (d, J=7.5 Hz, 1H), 12.44 (br s, 1 H). 13C NMR (DMSO-d6): δ 14.25 (CH3), 14.29 (CH3), 22.30 (CH2), 22.42 (CH2), 26.33 (CH2), 27.36 (CH2), 31.26 (CH2), 31.28 (CH2), 39.59 (CH2), 110.46 (CH), 119.72 (C), 120.62 (CH), 123.41 (CH), 131.73 (CH), 143.22 (C═N), 161.01 (C═O). HRMS (ES+) calcd for C20H30N3O2 (M+H+), m/e, 344.2335; found, 344.2333.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-339f21bc6ba54e7e97037d901bc8536d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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