Isatin → HCID 178444728, compound

HRID 1876252Notes

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

Participants

Reactant 2

HCID 7054Isatin

HCID 767924-Methoxybenzohydrazide

Product 1

HCID 178444728HCID 178444728, compoundYield 79%

Procedure

The title compound was prepared as a yellow solid, using isatin 3 and 4-methoxybenzhydrazide according to the synthetic method E. The resulting solid was washed with ethanol. Yield: 79%. 1H NMR (DMSO-d6): δ 0.85 (t, J=6.9 Hz, 3H), 1.26-1.36 (m, 6H), 1.65 (m, 2H), 3.79 (t, J=7.2 Hz, 2H), 3.87 (s, 3H), 7.14-7.24 (m, 4H), 7.48 (t, J=7.8 Hz, 1H), 7.65 (d, J=7.5 Hz, 1H), 7.89 (d, J=9 Hz, 2H), 13.86 (br s, 1H). 13C NMR (DSMO-d6): δ 14.33 (CH3), 22.43 (CH2), 26.39 (CH2), 27.41 (CH2), 31.32 (CH2), 39.77 (CH2), 56.07 (O—CH3), 110.63 (CH), 114.97 (CH), 119.76 (C), 121.13 (CH), 123.64 (CH), 124.46 (C), 129.98 (CH), 132.02 (CH), 143.30 (C═N), 161.63 (C═O), 163.68 (C═O). HRMS (ES+) calcd for C22H26N3O3 (M+H+), m/e, 380.1974; found, 380.1969.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-e1429ea7e6254c388d956334509e9d36
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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