2-(Ethylamino)-6fluoro-3-nitropyridine → 3-Amino-2-(ethylamino)-6-fluoropyridine

HRID 2229314Notes

Reaction equation

HRID 2229314 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([F:13])[N:5]=1)[CH3:2]>C1COCC1.[OH-].[OH-].[Pd+2]>[NH2:10][C:9]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]([F:13])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 184666162-(Ethylamino)-6fluoro-3-nitropyridine

Product 1

HCID 184666123-Amino-2-(ethylamino)-6-fluoropyridineYield 101.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(ethylamino)-6-fluoro-3-nitropyridine (43.2 g, 230 mmol) in THF (1 L) was stirred overnight at room temperature under hydrogen (1 atm.) in the presence of 20% Pd(OH)2/C (4.35 g). The catalyst was removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure to give the title compound (36.3 g, 95% yield) as a black solid.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-79863259f1654f0594532cd1c1a0da14
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

Loading…