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Water → 3-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-propan-1-ol

HRID 229017
Notes
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Reaction equation

HRID 229017 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][CH2:14][C:15](OCC)=[O:16])[N:9]=[CH:8][CH:7]=[C:6]2[O:20][C:21]1[C:22]([CH3:31])=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][CH2:14][CH2:15][OH:16])[N:9]=[CH:8][CH:7]=[C:6]2[O:20][C:21]1[C:22]([CH3:31])=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 68829564Ethyl 3-[6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-propionate

Product 1

HCID 577564903-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-propan-1-olYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

Ethyl 3-[6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-propionate (80 mg) was dissolved in tetrahydrofuran (5 ml) to prepare a solution. A diisobutylaluminum hydride/0.93 M hexane solution (1 ml) was added to the solution under ice cooling, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give the title compound (50 mg, yield 69%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3d9c3f8ffeb54d9ea2e4dafa2b1a6e0f
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes