4-Nitrobenzaldehyde → N-(3-Hydroxymethylphenyl)-alpha-(4-nitrophenyl)nitrone

HRID 845590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 845590
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][OH:10])[CH:6]=[CH:7][CH:8]=1.[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12]>>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:10])=[CH:18][C:17]2[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

3

Edukt 2

HCID 5414-NitrobenzaldehydeHCID 20131568N-(3-Hydroxymethylphenyl)hydroxylamine

Produkt 1

HCID 86742277N-(3-Hydroxymethylphenyl)-alpha-(4-nitrophenyl)nitroneAusbeute 81 %

Versuchsvorschrift

The reaction of hydroxylamine 91 (1.36 g, 10 mmol) with 4-nitrobenzaldehyde (58) (1.51 g, 10 mmol) afforded, after workup, a red solid. The crude product was recrystallized from acetone/petroleum ether to obtain 2.21 g (8.1 mmol, 81%) of 93 as a red crystalline solid: mp 207°-209° C.; IR (Nujol) 3260, 1590, 1555, 1510, 1320, 1150, 1020, 860 cm-1 ; 1H NMR (Me2SO-d6) δ 4.60 (d, J=5.6 Hz, 2H), 5.43 (t, J=5.7 Hz, 1H), 7.49-8.71 (m, 9H); 13C NMR (Me2SO-d6) δ 62.85, 119.99, 120.38, 124.29, 128.83, 129.47, 129.96, 132.70, 137.36, 144.79, 147.83, 148.94. Anal. Calcd for C14H12N2O4 : C, 61.76; H, 4.41. Found: C, 62.09; H, 4.59.

Aufarbeitung

  1. customafforded
  2. customThe crude product was recrystallized from acetone/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-2e33890bafa248eb8d53b903fdb3f751
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04758669

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