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Sodium Iodide → 2-Fluoro-4-[(6-methoxy-7-(3-morpholinopropyl)-4-quinolyl)oxy]aniline

HRID 31152
Notes
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Reaction equation

HRID 31152 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([CH2:22][CH2:23][CH2:24]Cl)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:26](=[O:29])([O-])[O-].[K+].[K+].[I-].[Na+].FC1C=CC([CH2:41][C:42](O)=O)=CC=1.[CH3:45][N:46](C)C=O>C(Cl)(Cl)Cl.CO>[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([CH2:22][CH2:23][CH2:24][N:46]4[CH2:45][CH2:26][O:29][CH2:42][CH2:41]4)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 98372-(4-Fluorophenyl)acetic acidHCID 11430Potassium CarbonateHCID 671970732-Fluoro-4-[(7-(3-chloropropyl)-6-methoxy-4-quinolyl)oxy]aniline

Product 1

HCID 67196640
2-Fluoro-4-[(6-methoxy-7-(3-morpholinopropyl)-4-quinolyl)oxy]aniline
Yield 76%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
70 °C

Procedure

The aniline compound (0.7 g) prepared in step 1) was dissolved in dimethylformamide (40 ml) to prepare a solution. Potassium carbonate (1.4 g), sodium iodide (0.6 g) and moripholine (0.85 g) (starting compound B) were added to the solution, and the mixture was stirred at 70° C. for 20 hr. The reaction solution was extracted with ethyl acetate, followed by washing with saturated brine. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under the reduced pressure. The residue was purified by column chromatography on silica gel, and the title compound (0.64 g, yield 76%) was obtained from the fraction of chloroform:methanol (95:5).

Workup

  1. customto prepare a solution
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washby washing with saturated brine
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-84cc826f0b834b4a8d693567a5418566
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425564B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes