Benzoylhydrazine → HCID 178523950, compound

HRID 1876260Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=O)[C:8]2=[O:9])=[CH:4][CH:3]=1.[C:20]([NH:28][NH2:29])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)/[C:10](=[N:29]/[NH:28][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)/[C:8]2=[O:9])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 11955Benzoylhydrazine

HCID 2779901-(4-Chlorobenzyl)-1H-indole-2,3-dione

Product 1

HCID 178523950HCID 178523950, compoundYield 86%

Procedure

The title compound was prepared as a yellow solid, using 1-(4-chlorobenzyl)-isatin and benzhydrazide according to the synthetic method D. The resulting solid was purified by crystallization in ethyl alcohol. Yield: 86%. 1H NMR (DMSO-d6): δ 5.03 (s, 2H), 7.08 (d, J=7.8 Hz, 1H), 7.18 (t, J=7.5 Hz, 1H), 7.39-7.47 (m, 5H), 7.60-7.74 (m, 4H), 7.94 (m, 2H), 13.84 (br s, 1H). 13C NMR (DMSO-d6): δ 42.43 (CH2), 110.97 (CH), 119.87 (C), 121.35 (CH), 123.99 (CH), 127.93 (CH), 129.15 (CH), 129.70 (CH), 129.88 (CH), 132.14 (CH), 132.45 (C), 132.78 (C), 133.44 (CH), 135.15 (C), 143.04 (C═N), 161.74 (C═O). HRMS (ES+) calcd for C22H17N3O2Cl (M+H+), m/e, 390.1018; found, 390.1004.

Workup

customThe resulting solid was purified by crystallization in ethyl alcohol

Sources & evidence

ORD record: ord-39e6cdfb3aaf437f9259244a6035105a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

Loading…