Hydrochloric Acid → 3-Chloropyridazine-4-carboxylic acid

HRID 2076834Notes

Reaction equation

HRID 2076834 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 217807723-Chloropyridazine-4-carboxylic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-824b4cce6b7f4bc08ffb9369b1e89944
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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