Sodium hydride → 6-(2-Methylpyridin-3-yloxy)pyridazine-3-carboxylic acid ethyl ester

HRID 840550

Reaktionsgleichung

Reaktionsgleichung von HRID 840550
[H-].[Na+].[OH:3][C:4]1[C:5]([CH3:10])=[N:6][CH:7]=[CH:8][CH:9]=1.[CH2:11]([O:13][C:14]([C:16]1[N:17]=[N:18][C:19](Cl)=[CH:20][CH:21]=1)=[O:15])[CH3:12]>CN(C=O)C>[CH2:11]([O:13][C:14]([C:16]1[N:17]=[N:18][C:19]([O:3][C:4]2[C:5]([CH3:10])=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH:20][CH:21]=1)=[O:15])[CH3:12]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 707192-Methylpyridin-3-olHCID 10352425Ethyl 6-chloropyridazine-3-carboxylate

Produkt 1

HCID 544471436-(2-Methylpyridin-3-yloxy)pyridazine-3-carboxylic acid ethyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (0.21 g of an 80% dispersion in oil, 7.0 mmol) was added to a solution of 3-hydroxy-2-methylpyridine (0.88 g, 8.0 mmol) in DMF (15 ml). After 1.5 h at r.t. a solution of 6-chloropyridazine-3-carboxylic acid ethyl ester (Chem. Pharm. Bull. 1994, 42(2), 371) (1.0 g, 5.4 mmol) in DMF (10 ml) was added and the mixture was stirred for a further 1.5 h. The DMF was removed in vacuo and the residue partitioned between dil. aq. NaOH (50 ml) and CH2Cl2 (100 ml). After drying (Na2SO4) the organics were evaporated to give the title compound as an off-white solid (1.09 g, 78%).

Aufarbeitung

  1. customThe DMF was removed in vacuo
  2. customthe residue partitioned between dil. aq. NaOH (50 ml) and CH2Cl2 (100 ml)
  3. dry with materialAfter drying (Na2SO4) the
  4. customorganics were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-694340372c0f4998a5679fd0a7b14521
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369060B1

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