Isoniazid → 3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole

HRID 2102293

Reaktionsgleichung

Reaktionsgleichung von HRID 2102293
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=O.[C:7]([NH:15][NH2:16])(=O)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1>C(Cl)Cl>[N:11]1[CH:12]=[CH:13][C:8]([C:7]2[N:1]3[CH2:5][CH2:4][CH2:3][C:2]3=[N:16][N:15]=2)=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 3767IsoniazidHCID 120252-Pyrrolidone

Produkt 1

HCID 8531463-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazoleAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Me3OBF4 (2.66 g, 18 mmol) was added to a solution of 2-pyrollidinone in DCM (150 ml) and the reaction mixture was stirred for 24 h. The reaction mixture was washed with aq. sat. NaHCO3, dried and concentrated. The residue was dissolved in EtOH (4 ml) and isonicotinic hydrazide (1.37 g, 10 mmol) was added. The mixture was heated in a microwave reactor for 1 h at 120° C. The volatiles were removed and the crude product purified with column chromatography (DCM/MeOH 20:1) to give 319 mg (11%) of the title compound. 1H NMR: 2.87 (m, 2H), 3.05 (t, 2H), 4.28 (t, 2H), 7.72 (d,2H), 8.72 (d, 2H).

Aufarbeitung

  1. washThe reaction mixture was washed with aq. sat. NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOH (4 ml)
  5. customThe volatiles were removed
  6. customthe crude product purified with column chromatography (DCM/MeOH 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-abaf5ea9dffc43dba276908e4574fe5c
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576077B2

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