4-(3-Fluoro-4-nitrophenoxy)-6-methoxy-7-(phenylmethoxy)quinoline → HCID 135674219, compound

HRID 1008331Notes

Reaction equation

HRID 1008331 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[C:22]([F:29])[CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1.[H][H]>CN(C)C=O.C(N(CC)CC)C.[OH-].[Pd+2].[OH-]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:30][CH3:31])[CH:11]=3)[N:16]=[CH:15][CH:14]=2)=[CH:21][C:22]=1[F:29]

Participants

6

Reactant 2

HCID 226671344-(3-Fluoro-4-nitrophenoxy)-6-methoxy-7-(phenylmethoxy)quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 135674219HCID 135674219, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

7-(Benzyloxy)-4-(3-fluoro-4-nitrophenoxy)-6-methoxyquinoline (190 mg) was dissolved in N,N-dimethylformamide (5 ml) and triethylamine (1 ml). Palladium hydroxide (40 mg) was added to the solution, and the mixture was stirred in a hydrogen atmosphere at room temperature overnight. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel by development with chloroform/methanol (20/1) to give 75 mg (yield 56%) of the title compound.

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. customThe residue was purified by thin-layer chromatography on silica gel by development with chloroform/methanol (20/1)

Sources & evidence

ORD record
ord-ad91409be7dc43c4ad65b3bf73700457
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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