Ethyl 2-amino-3-(hydroxy(oxido)amino)benzoate → HCID 18355136, Verbindung

HRID 1533797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1533797
[N+:1]([C:4]1[C:5]([NH2:15])=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:3])=[O:2].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>CN(C)C1C=CC=CC=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[N+:1]([C:4]1[C:5]([NH:15][C:16]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[O:23])=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:3])=[O:2]

Komponenten

6

Edukt 2

HCID 393670Ethyl 2-amino-3-(hydroxy(oxido)amino)benzoateHCID 417436Pyridine-4-carbonyl chloride

Produkt 1

HCID 18355136HCID 18355136, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 949N,N-DimethylanilineLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-nitro-2-aminobenzoate (700 mg) in N,N-dimethylaniline (7 ml) was added dropwise isonicotinoyl chloride (2.96 g) at 120° C. for 3 hours. After cooling, the reaction mixture was diluted with ethyl acetate and saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and washed with brine. The solution was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1) to give ethyl 3-nitro-2-(4-pyridyl)carbonylaminobenzoate (200 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-84c4dc68cc51443997fc16e98c450fa2
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207693B1

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