Toluene → Diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioate

HRID 1719940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719940
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])([O-])=O.C1(C)C=CC=CC=1>CN(C)C=O.[Pd].[H][H]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

6

Edukt 2

HCID 1140TolueneHCID 13060485Diethyl[(6-nitro-4-quinazolinylamino)methylene]propanedioate

Produkt 1

HCID 20266113Diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioateAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 178418361HCID 178418361, VerbindungLösungsmittel

Versuchsvorschrift

A suspension of diethyl [(6-nitro-4-quinazolinylamino)methylene]propanedioate (2.8 g) in N,N-dimethylformamide (152 ml) was shaken with 10% palladium on carbon (0.93 g) in hydrogen atmosphere at ambient temperature for an hour. After the reaction was completed, the catalyst was removed by filtration and washed with chloroform. The combined filtrate and washing was concentrated under reduced pressure to give a residue, to which was added toluene and concentrated under reduced pressure. This operation was repeated to give crystalline diethyl [(6-amino-4-quinazolinylamino)methylene]propanedioate (2.50 g).

Aufarbeitung

  1. customthe catalyst was removed by filtration
  2. washwashed with chloroform
  3. washThe combined filtrate and washing
  4. concentrationwas concentrated under reduced pressure
  5. customto give a residue
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-75e9ac969c9646b4b84c07b958786e63
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04543356

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