Water → HCID 21696643, compound

HRID 378794Notes

Reaction equation

HRID 378794 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([Cl:13])([Cl:12])[Cl:11])[CH:3]=1.[N-:14]=[N+]=[N-].[Na+].O.[BH4-].[Na+]>CN(C=O)C.CO>[NH2:14][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([Cl:13])([Cl:12])[Cl:11])[CH:3]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 33557Sodium AzideHCID 1168892,3,4-Trichloro-6-(trichloromethyl)pyridineHCID 4311764Sodium borohydride

Product 1

HCID 21696643HCID 21696643, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

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.

Workup

  1. extractionextracted (3x) with Et2O
  2. concentrationOrganic layer was concentrated
  3. customto yield a white solid, which
  4. extractionextracted (3×) with Et2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe resulting solid was washed several times with hexane

Sources & evidence

ORD record
ord-c1afc0992e30408aa87e0b5eb2cdbd91
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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