Acetic Acid → Methyl 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate

HRID 877411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877411
O=[C:2]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:3](OC)=[O:4].O.[NH2:14][NH2:15].CC(O)=O>CO.C1(C)C=CC=CC=1>[O:4]=[C:3]1[NH:15][N:14]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:2]1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 25775Dimethyl alpha-ketoglutarate

Produkt 1

HCID 12081646Methyl 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Dimethyl 2-oxoglutarate (1.5 g, 8.98 mmol) was dissolved in MeOH (62 mL). Hydrazine monohydrate (500 mg, 9.88 mmol) and AcOH (540 mg, 8.98 mmol) were added to the solution sequentially. The reaction mixture was warmed at 70° C. for 18 h. The solution was cooled and reduced to a residue which was subsequently redissolved in toluene and evaporated to afford an off-white solid. The solid was tritrated with hexanes and needed no further purification (1.2 g, 100%): 1H NMR (CDCl3, 600 MHz) δ 8.75 (s, 1H), 3.90 (s, 3H), 2.93 (t, 2H, J=8.5 Hz), 2.58 (t, 2H, J=8.5 Hz).

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customevaporated
  3. customto afford an off-white solid
  4. customno further purification (1.2 g, 100%)

Quellen und Nachweise

ORD-Eintrag
ord-49e4f47e46034af4a7d88308f3ea8212
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987312B2

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