4-Fluorobenzylamine → N-(4-fluorobenzyl)-3-nitro-2-pyridinamine

HRID 2109869Notes

Reaction equation

HRID 2109869 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:17][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 27628172-Fluoro-3-nitropyridine

Product 1

HCID 3647990N-(4-fluorobenzyl)-3-nitro-2-pyridinamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-fluoro-3-nitropyridine (2.5 g, 17.6 mmol), 4-fluorobenzyl-amine (4.40 g, 35.2 mmol), and N,N-diisopropyl-N-ethylamine (4.55 g, 35.2 mmol) in anhydrous acetonitrile (30 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated under vacuum, and the residue partitioned between water and ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 15% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the 2-(4-fluorobenzylamino)-3-nitropyridine intermediate as yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue partitioned between water and ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-9abb75fcf5824152b36bd637c1eba8ed
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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