m-Toluohydrazide → HCID 136359954, Verbindung

HRID 1019442

Reaktionsgleichung

Reaktionsgleichung von HRID 1019442
[Cl:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([NH:17][NH2:18])=[O:16]>C(O)C>[Cl:1][C:2]1[C:3]([OH:10])=[C:4]([CH:5]=[N:18][NH:17][C:15](=[O:16])[C:14]2[CH:19]=[CH:20][CH:21]=[C:12]([CH3:11])[CH:13]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 83082m-ToluohydrazideHCID 5196513-Chloro-2-hydroxybenzaldehyde

Produkt 1

HCID 136359954HCID 136359954, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of 3-chloro-2-hydroxy-benzaldehyde (0.100 g, 0.639 mmol) and 3-methyl-benzoic acid hydrazide (0.096 g, 0.639 mmol) in ethanol (2 mL) was heated to 60° C. for 18 hours. The reaction mixture was cooled to room temperature to precipitate the product. The solid was collected via suction filtration and rinsed with ethanol to furnish 3-methyl-benzoic acid [1-(3-chloro-2-hydroxy-phenyl)-methylidene]-hydrazide as a white solid (0.046 g, 25%): mp 166-169° C.; 1H NMR (400 MHz, CDCl3) δ 8.59 (d, J=12.0 Hz, 1H), 7.76 (d, J=10.0 Hz, 2H), 7.47 (dd, J=15.6, 6.2 Hz, 4H), 6.97 (t, J=7.8 Hz, 1H), 2.39 (d, J=12.0 Hz, 3H); ESIMS m/z 289 ([M+H]+), 287 ([M−H]−).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto precipitate the product
  3. filtrationThe solid was collected via suction filtration
  4. washrinsed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9b3d0a7bc62b4062b720883f8e3fb3ad
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08715745B2

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