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

HRID 2035574Notes

Reaction equation

HRID 2035574 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-e8a7d3cf71404939aa765911e8f5fe75
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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