Quinoxaline-6-carbonyl chloride → Quinoxaline-6-carboxaldehyde

HRID 2261093Notes

Reaction equation

HRID 2261093 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](Cl)=[O:12])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>COCCOC.CCOC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 2776328Quinoxaline-6-carbonyl chlorideHCID 16684435Lithium tritertbutoxyaluminohydride

Product 1

HCID 763958Quinoxaline-6-carboxaldehydeYield 73%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 1 l 3-neck flask under argon was placed Quinoxaline-6-carbonyl chloride in 600 ml of DME. To this solution was added lithium tri-tert-butoxyaluminohydride (1 eq.) at −78° C. over 1.5 h. The reaction was kept at that temperature for 5 h. Then ice was added, and the reaction was diluted with AcOEt and filtrated over celite. The two layers were separated and the organic phase was washed with NaHCO3 sat. Quinoxaline-6-carbaldehyde was obtained upon evaporating the solvent in 73% yield as yellowish solid.

Workup

  1. customIn a 1 l 3-neck flask under argon was placed
  2. additionThen ice was added
  3. filtrationfiltrated over celite
  4. customThe two layers were separated
  5. washthe organic phase was washed with NaHCO3 sat. Quinoxaline-6-carbaldehyde
  6. customwas obtained
  7. customupon evaporating the solvent in 73% yield as yellowish solid

Sources & evidence

ORD record
ord-1d4c3883e1914f32958bfcf48f5aa66b
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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