HCID 68089188, compound → HCID 86667806, compound

HRID 1772003Notes

Reaction equation

HRID 1772003 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[N:13][C:14]=3[C:5]=2[N:4]=[C:3]1[CH2:15][OH:16]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[N:13][C:14]=3[C:5]=2[N:4]=[C:3]1[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 68089188HCID 68089188, compound

Product 1

HCID 86667806HCID 86667806, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-methyl-3H-imidazo[4,5-h]quinolin-2-yl)methanol (560 mg, 2.62 mmol) in DCM (10 mL) was added manganese (IV) oxide (2.28 g, 26.2 mmol). The mixture was stirred at room temperature for 12 h. The solid was removed by filtration and the filtrate was concentrated. The crude product was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 2:1) to give 3-methyl-3H-imidazo[4,5-h]quinoline-2-carbaldehyde as a yellow solid (370 mg, yield: 67.5%). ESI MS: m/z 212 [M+H]+.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by silica gel column chromatography (
  4. washeluting with PE/EtOAc v/v 2:1)

Sources & evidence

ORD record
ord-d0b0bd73fd6041d8be3679470a9c179e
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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