Reaction #68414

Reaction equation

NH3.H2O

(2,6-dichloro-5-fluoropyridin-3-yl)methanamine

Compound 144

(2,6-dichloro-5-fluoropyridin-3-yl)methanamine

→

title compound

(5-Fluoropyridin-3-yl)methanamine

Solvents

MeOH

Conditions

Workup

1. 1
   OtherTo a Parr reaction bottle
2. 2
   Filtrationfiltered
3. 3
   Concentrationconcentrated
4. 4
   Extractionextracted with EtOAc (×3)
5. 5
   WashThe combined organic layer was washed with brine
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   workup.DISTILLATIONThe crude product was purified by distillation under vacuum

Procedure

To a Parr reaction bottle was added Pd—C (10%, 560 mg, 0.52 mmol), followed by 28% NH3.H2O (50 ml) and a solution of (2,6-dichloro-5-fluoropyridin-3-yl)methanamine (Compound 144, 10.1 g, 52 mmol) in MeOH (100 ml). The mixture was placed under 51 psi H2 on a shaker type Parr apparatus for 16 h, filtered and concentrated. The resulting aqueous solution was basified with NaOH, extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by distillation under vacuum to yield the title compound as colorless oil.

Source