Hydrochloric Acid → 3-Chloropyridazine-4-carboxylic acid

HRID 2076834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076834
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[N:8][C:7]=1[Cl:12])=[O:5])C.[Li+].[OH-].Cl>C1COCC1>[Cl:12][C:7]1[N:8]=[N:9][CH:10]=[CH:11][C:6]=1[C:4]([OH:5])=[O:3]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14542887Ethyl 3-chloropyridazine-4-carboxylate

Produkt 1

HCID 217807723-Chloropyridazine-4-carboxylic acidAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of crude 3-chloro-pyridazine-4-carboxylic acid ethyl ester (565 mg) in THF (5 ml) was added 2N LiOH (3.03 ml, 6.06 mmol) and the mixture was stirred for 15 min at ambient temperature. The pH of the reaction mixture was then adjusted to 2 by addition of 0.1N HCl and the mixture was extracted five times with ethyl acetate. The combined extracts were dried (Na2SO4) and evaporated to give the crude title compound as a brown solid (452 mg, 94%) which was used in the next reaction step without further purification. 1H NMR (d6-DMSO): 8.07 (d, J=5 Hz, 1H), 9.41 (d, J=5 Hz, 1H), 14.52 (s br, 1H).

Aufarbeitung

  1. extractionthe mixture was extracted five times with ethyl acetate
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-824b4cce6b7f4bc08ffb9369b1e89944
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928106B2

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