N-(4-fluorobenzyl)-3-nitro-2-pyridinamine → HCID 677108, compound

HRID 2109870Notes

Reaction equation

HRID 2109870 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

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

Product 1

HCID 677108HCID 677108, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(4-fluorobenzylamino)-3-nitropyridine (1.0 g, 4.05 mmol) and 10% Pd/C (0.3 g) in methanol (50 mL) was stirred under an atmosphere of hydrogen (1 atm) at room temperature for 5 hours. The product mixture was filtered through a pad of Celite, and concentrated under vacuum. The residual methanol was removed by co-evaporation with benzene. The resultant N2-(4-Fluorobenzyl)pyridine-2,3-diamine was used in the following step without further purification.

Workup

  1. filtrationThe product mixture was filtered through a pad of Celite
  2. concentrationconcentrated under vacuum
  3. customThe residual methanol was removed by co-evaporation with benzene
  4. customThe resultant N2-(4-Fluorobenzyl)pyridine-2,3-diamine was used in the following step without further purification

Sources & evidence

ORD record
ord-ede2666f14cc488595d856e3f767f11b
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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