HCID 13922984, compound → HCID 15672393, compound

HRID 2255204Notes

Reaction equation

HRID 2255204 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH:5]=[C:6]([C:16](OCC)=[O:17])[C:7]([CH3:15])=[N:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH:5]=[C:6]([CH:16]=[O:17])[C:7]([CH3:15])=[N:8]2

Participants

5

Reactant 2

HCID 13922984HCID 13922984, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15672393HCID 15672393, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 5,8-dimethoxy-2-methylquinoline-3-carboxylate (4.0 g, 0.0145 mol) in tetrahydrofuran is added to a slurry of lithium aluminum hydride (0.72 g, 0.019 mol) in ether. The reaction is stirred for 16 hours at 50° C. After cooling, the reaction is quenched by the sequential addition of water and 15% aqueous sodium hydroxide. Additional ether and anhydrous magnesium sulfate are added and the reaction mixture is filtered. The product is purified by chromatography using silica gel and ethyl acetate in hexanes as eluant. The resulting alcohol (1.50 g) is dissolved in methylene chloride and added to a slurry of pyridinium chlorochromate in methylene chloride. The resulting solution is stirred for 3 hours at room temperature. Diatomaceous earth is added, the reaction mixture is diluted with ether and filtered. The filtrate is concentrated in vacuo and the product purified by chromatography using silica gel and ethyl acetate in hexanes as eluant to yield the title compound (0.10 g, 5%) as a yellow solid, identified by IR and NMR spectral analysis.

Workup

  1. temperatureAfter cooling
  2. customthe reaction is quenched by the sequential addition of water and 15% aqueous sodium hydroxide
  3. additionAdditional ether and anhydrous magnesium sulfate are added
  4. filtrationthe reaction mixture is filtered
  5. customThe product is purified by chromatography
  6. dissolutionThe resulting alcohol (1.50 g) is dissolved in methylene chloride
  7. additionadded to a slurry of pyridinium chlorochromate in methylene chloride
  8. stirringThe resulting solution is stirred for 3 hours at room temperature
  9. additionDiatomaceous earth is added
  10. additionthe reaction mixture is diluted with ether
  11. filtrationfiltered
  12. concentrationThe filtrate is concentrated in vacuo
  13. customthe product purified by chromatography

Sources & evidence

ORD record
ord-7d6b45c7fc6343298616d8816d1ff50a
Source dataset
uspto-grants-1993_08
Patent number
US05239070

Reaction notes

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