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

HRID 1155996Notes

Reaction equation

HRID 1155996 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 etherchloroform 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-6fdf767be5064c9ab09ed1d714ac3f93
Source dataset
uspto-grants-1982_06
Patent number
US04333934

Reaction notes

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