4-Phenylsemicarbazide → 3-Hydroxy-2-[[(N-phenylaminocarbonyl)hydrazono]methyl]pyridine

HRID 486330

Reaktionsgleichung

Reaktionsgleichung von HRID 486330
[C:1]1([NH:7][C:8](=[O:11])[NH:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:12][C:13]1[C:14]([CH:19]=O)=[N:15][CH:16]=[CH:17][CH:18]=1>O.C(O)C>[OH:12][C:13]1[C:14]([CH:19]=[N:10][NH:9][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])=[N:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 108374-PhenylsemicarbazideHCID 27373323-Hydroxypicolinaldehyde

Produkt 1

HCID 1362071883-Hydroxy-2-[[(N-phenylaminocarbonyl)hydrazono]methyl]pyridineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

4-Phenyl semicarbazide (4.91 g, 33 mmol) was added to a suspension of 3-hydroxy-2-pyridine carbaldehyde (4.0 g, 33 mmol) in a mixture of ethanol water (30 mL:40 mL). The reaction mixture was stirred at room temperature for 3 h and the yellow product was collected by filtration. The yellow precipitate was washed with EtOH/H2O 1:1 and dried under P2O5 to yield 8.22 g (99%) of product. It can be recrystallized from EtOH/H2O; m.p. 201°-2° C. (dec.). 1H NMR (d6 -DMSO) δ: 10.85 (br.s., 1H); 10.6 (br.s., 1H); 9.14 (s, 1H); 8.27 (s, 1H); 8.15 (d of d, 1H); 7.55 (d, 2H); 7.26-7.36 (m, 4H); 7.01 (t, 1H).

Aufarbeitung

  1. filtrationthe yellow product was collected by filtration
  2. washThe yellow precipitate was washed with EtOH/H2O 1:1
  3. customdried under P2O5

Quellen und Nachweise

ORD-Eintrag
ord-1bee56f2f14144e0b3735674062c7c5c
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290942

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