2,6-Lutidine → HCID 86675935, compound

HRID 572687Notes

Reaction equation

HRID 572687 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=CC2C=CC=CC=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.CC1C=CC=C(C)N=1.I([O-])(=O)(=O)=[O:27].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[O:27])[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 86675934HCID 86675934, compound

Product 1

HCID 86675935HCID 86675935, compoundYield 47.7%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloro-2-methyl-4-styrylpyridazin-3(2H)-one (6 g, 24.32 mmol, Preparation #29), 4% aqueous osmium(VIII) oxide (0.1 mL, 1.216 mmol, Alfa-Aeser), 2,6-dimethylpyridine (5.21 g, 48.6 mmol, Aldrich) and sodium periodate (20.81 g, 97 mmol, Spectrochem) in aqueous dioxane (75%, 80 mL) was stirred at RT for about 3 h. The reaction mixture was diluted with water and the product extracted with EtOAc (5×60 mL). The combined organic layers were dried over sodium sulphate and evaporated under reduced pressure. The residue obtained was purified by silica gel (60-120) column chromatography by eluting with 30-50% EtOAc in hexane to afford 6-chloro-2-methyl-3-oxo-2,3-dihydropyridazine-4-carbaldehyde 2 g (47.7%) as pale yellow solid; 1H NMR (400 MHz, CDCl3) δ 10.359 (s, 1H), 7.658 (s, 1H), 3.846 (s, 3H); MS m/z: 170.9 (M−H)−

Workup

  1. extractionthe product extracted with EtOAc (5×60 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe residue obtained
  5. customwas purified by silica gel (60-120) column chromatography
  6. washby eluting with 30-50% EtOAc in hexane

Sources & evidence

ORD record
ord-5796a9f4311d48cdac1b0a24a18ca074
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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