6-Methylquinoline → 6-Quinolinecarbaldehyde

HRID 366362

Reaction equation

HRID 366362 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[Se]=[O:13]>C(OCC)(=O)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:1]=[O:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70596-MethylquinolineHCID 167175Oxyselenide

Product 1

HCID 7656536-QuinolinecarbaldehydeYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 6-methylquinoline (5.72 g, 40.0 mmol) and selenium oxide (4.44 g, 40.0 mmol) was heated to 220° C. for 1 h. After cooling down the residue was dissolved in ethyl acetate (100 mL). The organic solution was washed with brine, dried over MgSO4. Evaporation of solvents provided a solid, which was recrystalized from ether-hexane (1:1) mixture to give 6-quinolinecarboxaldehyde (3.45 g, 55%).

Workup

  1. temperatureAfter cooling down the residue
  2. washThe organic solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customEvaporation of solvents
  5. customprovided a solid, which
  6. customwas recrystalized from ether-hexane (1:1) mixture

Sources & evidence

ORD record
ord-f3598380d29a489bbfc56a171f17c70c
Source dataset
uspto-grants-2000_10
Patent number
US06130222

Linked notes

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