Acetonitrile → 2-ethyl-2H-indazole-4-carbaldehyde

HRID 1639771Notes

Reaction equation

HRID 1639771 reaction equation
[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH2:12][OH:13])=[N:4]1)[CH3:2].C[N+]1([O-])CCOCC1.C(#N)C>CC(O)C>[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH:12]=[O:13])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 82029Methyl morpholine oxideHCID 59334583(2-ethyl-2H-indazol-4-yl)methanol

Product 1

HCID 593345522-ethyl-2H-indazole-4-carbaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2-Ethyl-2H-indazol-4-yl)methanol (1.14 g, 6.47 mmol), 4 Å molecular sieves (550 mg), 4-methylmorpholine N-oxide (1.89 g, 16.2 mmol) and tetra-n-propylammonium perruthenate(VII) (114 mg, 0.323 mmol) were added to acetonitrile (70 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. 2-Propanol was added, and the mixture was stirred for 30 min. The mixture was filtered by silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→50/50) to give the title compound (820 mg, yield 73%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 min
  3. filtrationThe mixture was filtered by silica gel column chromatography (ethyl acetate)
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→50/50)

Sources & evidence

ORD record
ord-3423586e2e7c4f5da82f6b2315df9691
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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