2-Hydrazinopyridine → N-[(E)-(8-bromo-6-fluoroquinolin-2-yl)methylideneamino]pyridin-2-amine

HRID 339687Notes

Reaction equation

HRID 339687 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=O)[CH:8]=[CH:7]2.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][NH2:22]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([F:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](/[CH:12]=[N:22]/[NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=1)[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 86642345HCID 86642345, compound

Product 1

HCID 68558317N-[(E)-(8-bromo-6-fluoroquinolin-2-yl)methylideneamino]pyridin-2-amineYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-Bromo-6-fluoroquinoline-2-carbaldehyde (100 mg, 0.39 mmol) and 1-(pyridin-2-yl)hydrazine (43 mg, 0.39 mmol) were dissolved in 15 mL of absolute EtOH, and heated to reflux for 2 hours, at which time all starting material had been consumed. The reaction was then cooled to ambient temperature, and the yellow/orange product was collected by filtration (wash EtOH), affording (100 mg, 73.6% yield) as a yellow solid. MS APCI (+) m/z 345.1 and 347 (M+1 of each Br isotope) detected.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours, at which time all starting material
  3. customhad been consumed
  4. filtrationthe yellow/orange product was collected by filtration (wash EtOH)
  5. customaffording (100 mg, 73.6% yield) as a yellow solid

Sources & evidence

ORD record
ord-5bb622c2a60f4ecfa5c2fef4a2349868
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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