Acetic Anhydride → Methyl 4-acetamido-6-chloro-4'-(dimethylamino)-[1,1'-biphenyl]-3-carboxylate

HRID 2174549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174549
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([O:20][CH3:21])=[O:19].[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:10]=[CH:11][C:12]([N:15]([CH3:16])[CH3:17])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:24])[CH3:23]

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 68352236HCID 68352236, Verbindung2×

Produkt 1

HCID 68352041Methyl 4-acetamido-6-chloro-4'-(dimethylamino)-[1,1'-biphenyl]-3-carboxylateAusbeute 90,1 %

Versuchsvorschrift

Methyl 4-amino-6-chloro-4′-(dimethylamino)-[1,1′-biphenyl]-3-carboxylate (Intermediate 47) (2 g, 6.56 mmol) was dissolved in acetic anhydride (Aldrich, 6.75 mL, 92 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and the resulting precipitate was isolated by filtration and dried. The solid was triturated with methanol, filtered and dried to give the title compound methyl 4-acetamido-6-chloro-4′-(dimethylamino)-[1,1′-biphenyl]-3-carboxylate (2.05 g, 5.91 mmol, 90% yield) as beige solid. LCMS: (M+H)+=347; Rt=3.76 min.

Aufarbeitung

  1. customthe resulting precipitate was isolated by filtration
  2. customdried
  3. customThe solid was triturated with methanol
  4. filtrationfiltered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a8769168855341208f84bfa60d07191f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061998B2

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