Imidazo-[1,2-a]-quinoline-2-methanol → Imidazo[1,2-a]quinoline-2-carbaldehyde

HRID 1632197Notes

Reaction equation

HRID 1632197 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]2=[N:3][C:2]=1[CH2:14][OH:15])=[CH:10][CH:9]=[CH:8][CH:7]=3>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[CH:1]1[N:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]2=[N:3][C:2]=1[CH:14]=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 1

HCID 13770452Imidazo-[1,2-a]-quinoline-2-methanol

Product 1

HCID 13770453Imidazo[1,2-a]quinoline-2-carbaldehydeYield 81.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 4.2 g of imidazo-[1,2-a]-quinoline-2-methanol, 16.0 g of manganese dioxide and 11 ml of chloroform was refluxed for 4 hours and was then cooled overnight. The mixture was filtered through cellulose powder and the filter was washed with chloroform. The filtrate was evaporated to dryness under reduced pressure and the residue was triturated with diethyl ether to obtain 3.4 g of imidazo-[1,2-a]-quinoline-2-carboxaldehyde in the form of needles melting at 184°-185° C. after crystallization from an ether-chloroform mixture.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperaturewas then cooled overnight
  3. filtrationThe mixture was filtered through cellulose powder
  4. washthe filter was washed with chloroform
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-909ca12906e74fae83a02a78eec2e5dd
Source dataset
uspto-grants-1984_10
Patent number
US04474784

Reaction notes

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