Hydride → 8-Fluoroquinolin-4-amine

HRID 1608946Notes

Reaction equation

HRID 1608946 reaction equation
[N:1]([C:4]1[C:13]2[C:8](=[C:9]([F:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1)=[N+]=[N-].[BH4-].[Na+].[H-]>C(O)C>[NH2:1][C:4]1[C:13]2[C:8](=[C:9]([F:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 166653HydrideHCID 4311764Sodium borohydrideHCID 157905214-Azido-8-fluoroquinoline

Product 1

HCID 157905048-Fluoroquinolin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution at 15°-20° C. of 4-azido-8-fluoroquinoline in 12 mL of absolute ethanol was added a portion of 0.57 g (0.015 mol) of sodium borohydride. A powerful exotherm with vigorous evolution of gas was observed. The solution was cooled in ice and the remainder of the hydride was added in small portions within five minutes. The ice bath was then removed. After about two hours, the mixture was poured into about 200 mL of ice water. The precipitate was collected and air dried overnight. Yield 1.35 g. M.P. 184°-186° C.

Workup

  1. temperatureThe solution was cooled in ice
  2. customThe ice bath was then removed
  3. additionthe mixture was poured into about 200 mL of ice water
  4. customThe precipitate was collected
  5. customair dried overnight

Sources & evidence

ORD record
ord-270b9ec410a841399158ea7ee3967c68
Source dataset
uspto-grants-1995_03
Patent number
US05399564

Reaction notes

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