Water → 2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-propane-1,3-diol

HRID 228974Notes

Reaction equation

HRID 228974 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])[N:9]=[CH:8][CH:7]=[C:6]2[O:25][C:26]1[C:27]([CH3:36])=[N:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH:14]([CH2:20][OH:21])[CH2:15][OH:16])[N:9]=[CH:8][CH:7]=[C:6]2[O:25][C:26]1[C:27]([CH3:36])=[N:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 57756541Diethyl 2-[6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-malonate2×

Product 1

HCID 577564172-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-propane-1,3-diolYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl 2-[6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-malonate (compound 373) (50 mg) was dissolved in tetrahydrofuran (1 ml) to prepare a solution. Lithium aluminum hydride (10 mg) was added to the solution at 0° C., and the mixture was stirred at 0° C. for 3 hr and then at room temperature for 2 hr. Water was added to the reaction solution to stop the reaction. The mixture was filtered through Celite, water was then added to the filtrate, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (9.1 mg, yield 22%).

Workup

  1. customto prepare a solution
  2. waitat room temperature for 2 hr
  3. customthe reaction
  4. filtrationThe mixture was filtered through Celite, water
  5. additionwas then added to the filtrate
  6. extractionthe mixture was extracted with chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialwas then dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-69c76b390f694a5a9942e93b6260f91c
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…