Triethylamine → 2-(6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

HRID 575518

Reaktionsgleichung

Reaktionsgleichung von HRID 575518
[CH3:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=O.C(N(CC)CC)C.[C:31]1(=O)[CH2:36][CH2:35]CC[C:32]1=[O:37]>ClCCl.CN(C)C=O.CC(C)(O)C#N>[CH3:1][C:2]1[CH:3]=[C:4]([C:15]([CH:19]2[C:18](=[O:22])[CH2:35][CH2:36][CH2:31][C:32]2=[O:37])=[O:17])[C:5](=[O:14])[N:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Komponenten

8

Edukt 4

HCID 8471Triethylamine3×HCID 130061,2-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 127783026-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid

Produkt 1

HCID 867092642-(6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6406Acetone CyanohydrinKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid (0.56 g, 2.42 mmol) was stirred in anhydrous dichloromethane (13 ml) and 1 drop of anhydrous dimethylformamide was added. Oxalyl chloride (0.25 mL, 2.90 mmol) was added dropwise to the yellow solution. After 1.5 h the reaction was concentrated in vacuo. The residue obtained was dissolved in dichloromethane (20 ml). To the brown solution anhydrous triethylamine (1 ml), then cyclohexanedione (0.33 g, 2.90 mmol) was added, producing a reddish solution. A further 0.33 ml of anhydrous triethylamine was added. The reaction mixture was stirred at room temperature for 2 h (reaction monitored by LCMS), then acetone cyanohydrin (1 drop) and anhydrous triethylamine (0.67 ml) was added and the reaction was stirred overnight. LCMS indicated the desired product had been formed. The reaction mixture was concentrated in vacuo. The residue obtained was purified using column chromatography (SiO2, Toluene/Triethylamine/Dioxane/EtOH/Water 100:40:20:20:5 by volume) to afford the title compound as an orange oil (382 mg, 49%). 1H NMR (CDCl3) 2.05 (quin, 2H), 2.41 (m, 3H), 2.47 (br s, 2H), 2.73 (br s, 2H), 7.10 (s, 1H), 7.36 (m, 1H), 7.46 (m, 2H), 7.57 (m, 2H), 16.15 (br s, 1H) ppm.

Aufarbeitung

  1. concentrationAfter 1.5 h the reaction was concentrated in vacuo
  2. customThe residue obtained
  3. customproducing a reddish solution
  4. custom(reaction monitored by LCMS)
  5. stirringthe reaction was stirred overnight

Quellen und Nachweise

ORD-Eintrag
ord-46e8411cee534ac49063dd83c0820ef2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035049B2

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