Réaction #169856

Équation de réaction

water

4-(benzyloxy)aniline

2-chloro-5-fluoro-3-nitropyridine

K2CO3

→

title compound

Rendement 24.3%

N2-[4-(benzyloxy)phenyl]-5-fluoropyridine-2,3-diamine

Rendement 24.3%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with AcOEt
2. 2
   SéchageThe organic layer was dried over MgSO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   Filtrationcollected by filtration
5. 5
   workup.DISSOLUTIONThe obtained solid was dissolved in EtOH (20 mL)
6. 6
   workup.ADDITIONPt/C (2 g) was added
7. 7
   workup.STIRRINGUnder H2 atmosphere, the mixture was stirred for 1 h
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated
10. 10
    AutreThe residue was chromatographed on silica gel eluting with Hexane/AcOEt

Mode opératoire

A mixture of 4-(benzyloxy)aniline (2.26 g), 2-chloro-5-fluoro-3-nitropyridine (2 g) and K2CO3 (3.13 g) in DMF (20 mL) was stirred at 120° C. for 5 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was suspended in IPE and collected by filtration. The obtained solid was dissolved in EtOH (20 mL), and Pt/C (2 g) was added. Under H2 atmosphere, the mixture was stirred for 1 h, filtered and evaporated. The residue was chromatographed on silica gel eluting with Hexane/AcOEt to give the title compound (0.85 g).

Source