Sodium Hydroxide → HCID 22240240, compound

HRID 891944Notes

Reaction equation

HRID 891944 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH3:15])[N:6]=[N:7][CH:8]=1.[OH-].[Na+]>O1CCOCC1>[CH3:15][C:11]1[N:10]([CH2:9][C:5]2[NH:6][N:7]=[CH:8][C:3](=[O:2])[CH:4]=2)[CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22240134HCID 22240134, compound

Product 1

HCID 22240240HCID 22240240, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Methoxy-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine (4.25 g, 21 mmol) was dissolved in dioxane (65 ml) and 2N NaOH (42 ml) was added. The mixture was refluxed for 7 hours, cooled to room temperature and quenched with 2N HCl (65 ml). The pH was adjusted to 8 with saturated solution of NaHCO3. The solvent was removed in vacuo and the residue was taken in MeOH (100 ml). After filtration, the solvent was removed in vacuo and diluted with MeOH (50 ml). Silicagel (10 g) was added and the solvent was evaporated. The residue was chromatographed over silica gel (CH2Cl2—MeOH 9:1, 4:1, 2:1) to provide 6-(2-methyl-imidazol-1-yl-methyl)-1H-pyridazin-4-one (4.1 g, 100%) as a pale yellow solid, MS: m/e=191.3 (M+H+).

Workup

  1. temperatureThe mixture was refluxed for 7 hours
  2. customquenched with 2N HCl (65 ml)
  3. customThe solvent was removed in vacuo
  4. filtrationAfter filtration
  5. customthe solvent was removed in vacuo
  6. additiondiluted with MeOH (50 ml)
  7. additionSilicagel (10 g) was added
  8. customthe solvent was evaporated
  9. customThe residue was chromatographed over silica gel (CH2Cl2—MeOH 9:1, 4:1, 2:1)

Sources & evidence

ORD record
ord-962ec0bd8e8c47acbf29dbbb0b6a1e33
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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