7-Benzyloxy-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline → 6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol

HRID 228952Notes

Reaction equation

HRID 228952 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[C:21]([CH3:30])=[N:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:31][CH3:32])C1C=CC=CC=1>CN(C)C=O.[OH-].[Pd+2].[OH-]>[CH3:32][O:31][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[C:21]([CH3:30])=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2

Participants

4

Reactant 1

HCID 230785177-Benzyloxy-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline2×

Product 1

HCID 1358548286-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-olYield 85%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6228DimethylformamideSolvent

Procedure

7-Benzyloxy-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (compound 351) (1 g) was dissolved in N,N-dimethylformamide (15 ml) to prepare a solution. 20% Palladium hydroxide (100 mg) was added to the solution, and the mixture was stirred at room temperature under a hydrogen stream overnight. The reaction solution was filtered through Celite, and the solvent was removed from the filtrate by distillation under the reduced pressure. The residue was purified by column chromatography using chloroform-methanol to give the title compound (647 mg, yield 85%).

Workup

  1. customto prepare a solution
  2. filtrationThe reaction solution was filtered through Celite
  3. customthe solvent was removed from the filtrate by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-34cd52cace804acca87c6e2b0a228138
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…