2,4,6-Trimethylpyridine → HCID 178434191, compound

HRID 1700453Notes

Reaction equation

HRID 1700453 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:17][C:16]2[NH:15][N:14]=[C:13]([CH3:18])[C:12]=2[C:11](=[O:19])[CH2:10]1.[I-].[Li+].N1C(C)=CC(C)=CC=1C>>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:17][C:16]2[NH:15][N:14]=[C:13]([CH3:18])[C:12]=2[C:11](=[O:19])[CH2:10]1

Participants

4

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 178489315HCID 178489315, compound

Product 1

HCID 178434191HCID 178434191, compoundYield 18.9%

Procedure

A mixture of 6-(2-methoxyphenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (0.28 g), lithium iodide (0.44 g) and collidine (0.79 g) was refluxed for 5 hours. Under reduced pressure, collidine was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give, the residue was purified with silica gel column chromatography (EtOAc/hexane). The resulting crystals were recrystallized from acetone-hexane to give colorless crystals of 6-(2-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (0.05 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customUnder reduced pressure, collidine was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give
  8. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  9. customThe resulting crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-65cc17eb4ecb49929b62ce6ad2c40cfb
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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