HCID 178520030, compound → 5-chloro-1H-indazole-3-carbaldehyde

HRID 1749867Notes

Reaction equation

HRID 1749867 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][OH:12]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 178520030HCID 178520030, compound

Product 1

HCID 1785200295-chloro-1H-indazole-3-carbaldehydeYield 51.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (5-chloro-1H-indazol-3-yl)methanol (0.208 g, 1.14 mmol) in ethyl acetate (10 mL) was added with manganese dioxide (0.991 g, 11.4 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered through Celite, then the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 5-chloro-1H-indazole-3-carbaldehyde (0.106 g, 51%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-d0874be4f7f54238a129321dc68e4fcb
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…