Hydrochloric Acid → 3-Oxo-2-(pyridin-2-yl)-2,3-dihydropyridazine-4-carboxylic acid

HRID 2241417Notes

Reaction equation

HRID 2241417 reaction equation
CC1(C)[O:7][C:6](=[O:8])[C:5](=[CH:9]/[CH:10]=[N:11]/[NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:4](=O)[O:3]1.C[O-].[Na+].Cl>CO>[O:3]=[C:4]1[C:5]([C:6]([OH:7])=[O:8])=[CH:9][CH:10]=[N:11][N:12]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 87481543HCID 87481543, compound

Product 1

HCID 685120393-Oxo-2-(pyridin-2-yl)-2,3-dihydropyridazine-4-carboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (E)-2,2-dimethyl-5-(2-(2-(pyridin-2-yl)hydrazono)ethylidene)-1,3-dioxane-4,6-dione (0.050 g, 0.182 mmol) and NaOMe (0.0118 g, 0.218 mmol) in MeOH (6 mL) was heated under reflux for 15 hours. The salt was treated with cold 1 N HCl solution, extracted with DCM, dried over MgSO4, and concentrated to afford 17.6 mg (45%) of the desired product. LRMS (apci pos): 218 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. extractionextracted with DCM
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-92f10bab6e454b03b2adb331380a43aa
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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