Lithium Hydroxide → [4-Methyl-6-oxopyridazin-1(6H)-yl]acetic acid

HRID 887111Notes

Reaction equation

HRID 887111 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]([CH2:9][C:10]([O:12]CC)=[O:11])[C:6](=[O:8])[CH:7]=1.[OH-].[Li+].FC(F)(F)C(O)=O>O1CCCC1.CO.O>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([CH2:9][C:10]([OH:12])=[O:11])[C:6](=[O:8])[CH:7]=1

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 77231410ethyl [4-methyl-6-oxopyridazin-1(6H)-yl]acetate

Product 1

HCID 66939440[4-Methyl-6-oxopyridazin-1(6H)-yl]acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To ethyl [4-methyl-6-oxopyridazin-1(6H)-yl]acetate (0.575 g, 2.93 mmol) in tetrahydrofuran (3 mL), methanol (2 mL) and water (2 mL) was added 1 N lithium hydroxide solution (2.9 mL). The reaction mixture was stirred at ambient temperature for 1.5 h. After neutralized with trifluoro acetic acid, the reaction mixture was directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-45% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The pure fractions were lyophilized overnight to yield the title compound. LC/MS 169.2 (M+1).

Workup

  1. customthe reaction mixture was directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-45% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)
  2. waitThe pure fractions were lyophilized overnight

Sources & evidence

ORD record
ord-e372c6c011c44ef88c95a22c13288876
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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