Sodium Hydroxide → 1224639-98-8

HRID 1877362Notes

Reaction equation

HRID 1877362 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15](=O)[C:14]2=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[C:7]1([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH2:15][CH2:14]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 58599427HCID 58599427, compound

Product 1

HCID 204283391224639-98-8Yield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride (3.99 g, 105.0 mmol, 5.0 equiv) in THF (30 mL) was added slowly a solution of 1-phenyl-1,4-dihydro-quinoxaline-2,3-dione (5.00 g, 21.0 mmol, 1.0 equiv; prepared as described by S.-K. Lin Molecules 1996, 1, 37-40) in THF (50 mL). After heating the reaction mixture to reflux for 16 h, a solution of 1 M NaOH (100 mL) was added. The reaction mixture was stirred for a few minutes, MgSO4 added and then filtered over Celite. Extraction of the filter cake with ethyl acetate (3×100 mL) and evaporation of the solvent under reduced pressure provided the crude reaction product which was purified by silica column chromatography eluting with a gradient of heptane/ethyl acetate to afford 3.23 g (73%) of the title compound as an orange solid. MS (ED: 210.0 [M]+.

Workup

  1. temperatureAfter heating the reaction mixture
  2. temperatureto reflux for 16 h
  3. filtrationfiltered over Celite
  4. extractionExtraction of the filter cake
  5. customwith ethyl acetate (3×100 mL) and evaporation of the solvent under reduced pressure
  6. customprovided the crude
  7. customreaction product which
  8. customwas purified by silica column chromatography
  9. washeluting with a gradient of heptane/ethyl acetate

Sources & evidence

ORD record
ord-1d279c2e537b46edb385d2b019b75d9c
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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