Acetic Acid → 3-Methyl-benzoic acid [1-(3,5-dichloro-2-hydroxyphenyl)-ethylidene]-hydrazide

HRID 1399491Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=O)[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([NH:19][NH2:20])=[O:18].C(O)(=O)C>CCO>[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=[N:20][NH:19][C:17](=[O:18])[C:16]2[CH:21]=[CH:22][CH:23]=[C:14]([CH3:13])[CH:15]=2)[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 1-(3,5-dichloro-2-hydroxyphenyl)-ethanone (0.100 g, 0.49 mmol), 3-methylbenzoic acid hydrazide (0.069 g, 0.46 mmol), and glacial acetic acid (0.3 mL) in EtOH (3 mL) was heated to 60° C. for 4 h The reaction mixture was cooled to room temperature to precipitate the product. The solid was collected via suction filtration and rinsed with H2O to furnish the title material as a yellow solid (0.144 g, 93%): mp 221-223° C.; 1H NMR (400 MHz, DMSO) δ 14.48 (s, 1H), 11.54 (s, 1H), 7.79-7.72 (m, 2H), 7.68 (d, J=2.5 Hz, 1H), 7.64 (d, J=2.4 Hz, 1H), 7.47-7.42 (m, 2H), 2.52 (s, 3H), 2.41 (s, 3H); ESIMS m/z 337 ([M+H]+), 335 ([M−H]−).

Workup

temperaturewas cooled to room temperature
customto precipitate the product
filtrationThe solid was collected via suction filtration
washrinsed with H2O

Sources & evidence

ORD record: ord-e8b6900f53b14872953f96781f843b10
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906829B2

Reaction notes

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