7-Quinolinemethanol → 7-Quinolinecarboxaldehyde

HRID 326248Notes

Reaction equation

HRID 326248 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][OH:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1>[O-2].[Mn+4].[O-2].ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 976097-Quinolinemethanol

Product 1

HCID 47122557-QuinolinecarboxaldehydeYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.6 parts of 7-quinolinemethanol, 20 parts of manganese(IV)oxide and 130 parts of dichloromethane was stirred for 24 hours at room temperature. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2). The eluent of the desired fraction was evaporated, yielding 8 parts (94.2%) of 7-quinolinecarboxaldehyde; mp. 56° C. (interm. 1).

Workup

  1. filtrationThe reaction mixture was filtered over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2)
  4. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-c2909b5dbb8d4e4994c854d8f099dd41
Source dataset
uspto-grants-1993_12
Patent number
US05268380

Reaction notes

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