Benzeneacetic acid, hydrazide → (1E)-[2-(1-naphthylmethoxy)phenyl]methylene-2-phenylacetohydrazide

HRID 1795114

Reaktionsgleichung

[C:1]1([CH2:11][O:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH:15]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:21]1([CH2:27][C:28]([NH:30][NH2:31])=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCO>[C:1]1([CH2:11][O:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2/[CH:15]=[C:27](\[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[C:28]([NH:30][NH2:31])=[O:29])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 2-(1-naphthylmethoxy)benzaldehyde (300 mg, 1.14 mmol) in EtOH (10 mL) is added phenyl acetic hydrazide (172 mg, 1.14 mmol) and the reaction is heated to 80° C. for 1 h. While cooling a white precipitate forms, and this solid is isolated by filtration and washed with portions of EtOH and Et2O. This solid is dried under vacuum to provide N′-{(1E)-[2-(1-naphthylmethoxy)phenyl]methylene-2-phenylacetohydrazide (254 mg, 57%). 1H-NMR (400 MHz, DMSO-d6) 11.60–11.55 (m, 1H), 8.43–8.38 (m, 1H), 8.11–7.74 (m, 4H), 7.60–7.56 (m, 2H), 7.44–7.42 (m, 2H), 7.31–7.21 (m, 4H), 7.05–7.04 (m, 1H), 5.65–5.63 (m, 2H), 3.96 (s, 1H), 3.54 (s, 1H), 3.34 (s, 3H). ESI+ for C26H22N2O2 m/z 395 (M+H)+.

Aufarbeitung

temperatureWhile cooling a white precipitate forms
customthis solid is isolated by filtration
washwashed with portions of EtOH and Et2O
customThis solid is dried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-9081d92799004c2580866c8544d6cd88
Quelldatensatz: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07026339B2

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