2-Aminobenzyl alcohol → 2-Aminobenzaldehyde

HRID 1196555Notes

Reaction equation

HRID 1196555 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 214392-Aminobenzyl alcohol

Product 1

HCID 682552-AminobenzaldehydeYield 96.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

2-Aminobenzyl alcohol (ex. Aldrich) (2 g) was oxidised with activated manganese dioxide (2.7 g) in chloroform over 20 hours. After filtration and concentration the crude product was purified by column chromatography on silica (ethyl acetate) to give 2-aminobenzaldehyde (1.9 g) as a dark-red oil which was used directly. The latter in xylene (70 ml) was heated under reflux in a Dean-Stark apparatus with ethyl cyanoacetate (3.7 g) (ex. Aldrich) and piperidine (0.8 ml). Upon cooling the 2-hydroxy-3-cyanoquinoline was collected by filtration, washed with ether, dried and converted to the 2-chloro-3-cyanoquinoline.

Workup

  1. filtrationAfter filtration and concentration the crude product
  2. customwas purified by column chromatography on silica (ethyl acetate)

Sources & evidence

ORD record
ord-51686bef353d4930a57429ec0b330eb0
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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