4-Aminonicotinaldehyde → 2-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide

HRID 270693

Reaktionsgleichung

Reaktionsgleichung von HRID 270693
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([OH:15])=O.[NH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[CH:23]=[O:24]>S(Cl)(Cl)=O.ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([NH:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[CH:23]=[O:24])=[O:15]

Komponenten

6

Edukt 2

HCID 27610334-AminonicotinaldehydeHCID 542654372,6-Dichloro-3-nitrophenylacetic acid

Produkt 1

HCID 598338592-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamideAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of (2,6-dichloro-3-nitro-phenyl)-acetic acid (15.0 g, 60.0 mmol) in thionyl chloride (60 mL) is refluxed for one hour. The solvent is removed by concentration; dry toluene is added and concentrated to thoroughly remove thionyl chloride. To the solution of acid chloride in dry dichloromethane (200 mL) is added (drop-wise) a solution of 4-amino-pyridine-3-carbaldehyde (6.6 g, 54 mmol) in dichloromethane (50 mL) and DIEDA (10.7 mL, 60 mmol). The mixture is at room temperature for 2 hours. The reaction mixture is diluted with EtOAc (300 ml) and washed with saturated K2CO3 and brine. The organic layer is dried, filtered and concentrated to give crude product. Recrystallization with dichloromethane/hexane results in the titled compound as a solid (18.2 g, 95.2%).

Aufarbeitung

  1. customThe solvent is removed by concentration
  2. additiondry toluene is added
  3. concentrationconcentrated to thoroughly remove thionyl chloride
  4. washwashed with saturated K2CO3 and brine
  5. customThe organic layer is dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product
  9. customRecrystallization with dichloromethane/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c0ea74fc44c74a67a44b70cbc2269a15
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449582B2

Verknüpfte Notizen

Wird geladen…