3-Nitrobenzaldehyde → 2-(N-nicotinoylamino)ethyl 2-(3-nitrobenzylidene)acetylacetate

HRID 728321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728321
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].C([O-])(=O)C.[NH2+]1CCCCC1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH:16][C:14](=[O:15])[CH2:13][C:12]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1)=[O:17])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 3014295Piperidinium acetateHCID 10444784HCID 10444784, Verbindung

Produkt 1

HCID 539056402-(N-nicotinoylamino)ethyl 2-(3-nitrobenzylidene)acetylacetateAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 9.07 g (0.06 mole) of m-nitrobenzaldehyde, 15.0 g (0.06 mole) of 2-nicotinoylaminoethyl acetoacetate and 1.74 g (0.012 mole) of piperidinium acetate in 100 ml of benzene was heated at reflux under azeotropic dehydration conditions for 2 hours. After the reaction, the mixture was extracted with benzene, and the extract was washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave 19.82 g of 2-nicotinoylaminoethyl 3-nitrobenzilideneacetoacetate as white crystals.

Aufarbeitung

  1. temperatureat reflux under azeotropic dehydration conditions for 2 hours
  2. customAfter the reaction
  3. extractionthe mixture was extracted with benzene
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9ec2509816b34552a29a32a14b7f4cc3
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047543

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