Reaction #465976

Reaction equation

NaBH4

4,5,6-trichloro-2-trichloromethylpyridine

NaN3

H2O

H2O

→

4-amino-5,6-dichloro-2-trichloromethylpyridine

Yield 69.2%

Solvents

DMF

MeOH

Conditions

Workup

1. 1
   Extractionextracted (3x) with Et2O
2. 2
   ConcentrationOrganic layer was concentrated
3. 3
   Otherto yield a white solid, which
4. 4
   Extractionextracted (3×) with Et2O
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   WashThe resulting solid was washed several times with hexane

Procedure

To a solution of 4,5,6-trichloro-2-trichloromethylpyridine (2 g, 6.7 mmol) in aqueous DMF was added NaN3 (0.5 g, 7.7 mmol). The resulting mixture was heated at 70° C. for 2 hr, added to H2O and extracted (3x) with Et2O. Organic layer was concentrated to yield a white solid, which was dissolved in 10 mL of MeOH. Excess NaBH4 was added and the reaction mixture was stirred at room temperature for 0.5 hr. This material was added to H2O, extracted (3×) with Et2O, dried over MgSO4 and concentrated in vacuo. The resulting solid was washed several times with hexane to give 1.3 g of 4-amino-5,6-dichloro-2-trichloromethylpyridine.

Source