Nitric Acid → Acetamide, N-(3-nitro(1,1'-biphenyl)-4-yl)-

HRID 859063

Reaktionsgleichung

Reaktionsgleichung von HRID 859063
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[N+:24]([O-])([OH:26])=[O:25]>O>[N+:24]([C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])([O-:26])=[O:25]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 19998N-Acetyl-4-aminobiphenyl

Produkt 1

HCID 79364Acetamide, N-(3-nitro(1,1'-biphenyl)-4-yl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 4-acetamido-1,1′biphenyl (21.1 g, 0.1 mol) and 150 mL of acetic anhydride maintained between 8° C. and 13° C. is slowly added dropwise over 32 minutes 12.7 mL of 70% nitric acid. The reaction mixture is added to 600 mL of a mixture of water and ice and the resultant precipitate is collected by filtration. The filter cake is washed with water and the residue is recrystallized from methanol (800 mL) to give 23.6 g of the title compound as a yellow crystalline solid melting at 129–132° C.

Aufarbeitung

  1. temperaturemaintained between 8° C. and 13° C.
  2. filtrationthe resultant precipitate is collected by filtration
  3. washThe filter cake is washed with water
  4. customthe residue is recrystallized from methanol (800 mL)

Quellen und Nachweise

ORD-Eintrag
ord-981f186ace28470a9cf664caae25ecc3
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148274B2

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