Ethylamine → 2-(Ethylamino)-6fluoro-3-nitropyridine

HRID 2229313Notes

Reaction equation

HRID 2229313 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1.[CH2:12]([NH2:14])[CH3:13]>C1COCC1>[CH2:12]([NH:14][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1)[CH3:13]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 113895462,6-Difluoro-3-nitropyridine

Product 1

HCID 184666162-(Ethylamino)-6fluoro-3-nitropyridineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,6-difluoro-3-nitropyridine (45.7 g, 285 mmol) in THF (500 mL) at −40° C. was added drop-wise a solution of ethylamine (25.7 g, 570 mmol) in THF (250 mL). After 30 min, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The resulting yellow solid was purified by flash chromatography (15% EtOAc in hexane) to give the title compound (43.2 g, 82% yield) as a yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting yellow solid was purified by flash chromatography (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-e4cf6ec97e3a42d592211acb955df550
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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