2-Hydrazinopyridine → 6-Fluoro-2-((2-(pyridin-2-yl)hydrazono)methyl)-8-(triisopropylsilyloxy)quinoline

HRID 876408Notes

Reaction equation

HRID 876408 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:23]=O)[CH:6]=[CH:5]2.[NH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[NH2:26]>CCO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:23]=[N:26][NH:25][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 866386106-Fluoro-8-(triisopropylsilyloxy)quinoline-2-carbaldehyde

Product 1

HCID 672297076-Fluoro-2-((2-(pyridin-2-yl)hydrazono)methyl)-8-(triisopropylsilyloxy)quinolineYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Fluoro-8-(triisopropylsilyloxy)quinoline-2-carbaldehyde (15.0 g, 43.2 mmol) and 2-hydrazinylpyridine (4.71 g, 43.2 mmol) were combined in 100 mL of anhydrous EtOH, and stirred at ambient temperature over night. Following over night stirring, the desired product was collected by filtration (washing with cold EtOH), affording 6-fluoro-2-((2-(pyridin-2-yl)hydrazono)methyl)-8-(triisopropylsilyloxy)quinoline (14.0 g, 31.9 mmol, 74% yield) as a yellow-white powder.

Workup

  1. waitFollowing over night
  2. stirringstirring
  3. filtrationthe desired product was collected by filtration (washing with cold EtOH)

Sources & evidence

ORD record
ord-90ba65a3cfa5414c911f06d360fabc87
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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