p-Nitroacetophenone → HCID 88069650, Verbindung

HRID 991557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991557
[Cl:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=O.C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C(OC(=O)C)(=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[O:14][C:12](=[O:13])/[C:11](=[C:16](/[C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)\[CH3:15])/[N:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 7487p-NitroacetophenoneHCID 7918Acetic AnhydrideHCID 53558Glycine, N-(2-chloronicotinoyl)-HCID 178418268HCID 178418268, Verbindung

Produkt 1

HCID 88069650HCID 88069650, VerbindungAusbeute 20,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-{[(2-chloro-3-pyridinyl)carbonyl]amino}acetic acid (6.44 g, 30 mmol, prepared from glycine and 2-chloronicotinoyl chloride), 4-nitroacetophenone (2.48 g, 15 mmol), lead (IV) acetate (3.33 g, 7.5 mmol) and acetic anhydride in THF (30 ml) was heated at reflux for 4 days. The mixture was poured onto crushed ice, the solid filtered off, washed with water and dried. The brown solid was triturated twice with boiling ethanol and filtered off to give the title compound as a brown solid (1.07 g). δH (CDCl3), 8.57 (1H, dd, J 4.8, 2.1 Hz, PyH), 8.34-8,29 (3H, m, ArH+PyH), 8.05 (2H, d, J 9.1 Hz, ArH), 7.41 (1H, dd, J 7.9, 4.8 Hz, PyH) and 2.84 (3H, s, Me).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. additionThe mixture was poured
  4. customonto crushed ice
  5. filtrationthe solid filtered off
  6. washwashed with water
  7. customdried
  8. customThe brown solid was triturated twice with boiling ethanol
  9. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-4f34db70fe8f424a802c52c2d1c949a8
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465471B1

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