Nitric Acid → 4-Cyano-4'-(4-methoxycarbonylbutyrylamino)biphenyl

HRID 1598401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1598401
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H][H].C(C1C=CC(C2C=CC=CC=2)=CC=1)#N.[N+]([O-])(O)=O.C(N(C(C)C)C(C)C)C.[Cl-].[CH3:46][O:47][C:48](=[O:55])[CH2:49][CH2:50][CH2:51][C:52](O)=[O:53]>C(OCC)(=O)C.C(C1C=CC(C2C=CC([N+]([O-])=O)=CC=2)=CC=1)#N.C(Cl)Cl.[Pd]>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:52](=[O:53])[CH2:51][CH2:50][CH2:49][C:48]([O:47][CH3:46])=[O:55])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)#[N:15]

Komponenten

11

Edukt 6

HCID 944Nitric AcidHCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 81531DiisopropylethylamineHCID 971934-Amino-4'-cyanobiphenylHCID 53445129Glutaric acid monomethylester chlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 538293104-Cyano-4'-(4-methoxycarbonylbutyrylamino)biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 52001084-Cyano-4'-nitrodiphenylLösungsmittel2×

Versuchsvorschrift

6.6 g of 4-amino-4'-cyano-biphenyl (melting point: 171°-173° C., prepared by reduction of 4-cyano-4'-nitro-biphenyl with hydrogen in the presence of palladium/charcoal in ethyl acetate, 4-cyano-4'-nitro-biphenyl is prepared by reacting 4-cyano-biphenyl with fuming nitric acid) and 5.8 g of N-ethyl-diisopropylamine are dissolved in 70 ml of methylene chloride and 5.6 g of glutaric acid monomethylester chloride are added with stirring. The mixture is stirred for two hours at ambient temperature. The organic phase is washed successively with 0.1N sodium hydroxide solution, 0.1N hydrochloric acid and water. After evaporation of the organic phase the residue is recrystallized from ethanol.

Aufarbeitung

  1. customis prepared
  2. stirringThe mixture is stirred for two hours at ambient temperature
  3. washThe organic phase is washed successively with 0.1N sodium hydroxide solution, 0.1N hydrochloric acid and water
  4. customAfter evaporation of the organic phase the residue
  5. customis recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-35a81d3c95974a6bac05078ce77c4e53
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736559

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