Water → Ammonium Hydroxide

HRID 130725

Reaktionsgleichung

Reaktionsgleichung von HRID 130725
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].Cl[C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=1.O>CN(C=O)C>[NH4+:19].[OH-:1].[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=2)=[C:3]([CH3:10])[CH:4]=1)=[O:7]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 804566-ChloronicotinamideHCID 1399014-Hydroxy-3-methylbenzaldehyde

Produkt 2

HCID 14923Ammonium HydroxideAusbeute 0,7 %HCID 597302736-(4-Formyl-2-methyl-phenoxy)-nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-hydroxy-3-methylbenzaldehyde (1.0 equiv) in DMF (0.2 M solution) was treated with K2CO3 (1.5 equiv) and 6-chloronicotinamide (1.0 equiv). The reaction mixture was placed inside the microwave oven and then irradiated for 5 min. Upon completion of the reaction, the mixture was cooled, poured into H2O and extracted with ethyl acetate, and the combined organic layers were washed twice with water and brine. After drying the extracts over magnesium sulfate and evaporation under vacuum the crude product was purified by silica gel chromatography using CHCl3: EtOH 7%: NH4OH 0.7% to afford the title compound as a solid.

Aufarbeitung

  1. customirradiated for 5 min
  2. customUpon completion of the reaction
  3. temperaturethe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washthe combined organic layers were washed twice with water and brine
  6. customAfter drying the extracts
  7. customover magnesium sulfate and evaporation under vacuum the crude product
  8. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ac9f9a605430414ea11139c1849030e1
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381719B2

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