Ammonia → 1-(6-Chloropyridin-3-yl)ethan-1-amine

HRID 561015Notes

Reaction equation

HRID 561015 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[NH3:11].[BH4-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([NH2:11])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 157456051-(6-Chloropyridin-3-yl)ethan-1-amineYield 83.4%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

Stir a mixture of 1-(6-chloro-pyridin-3-yl)-ethanone (5 g, 32.14 mmol) in titanium tetra(isopropoxide) (18.27 g, 64.27 mmol) and ammonia (160.7 mmol, 2 M in MeOH) under N2 for 6 hours at room temperature. To this mixture add sodium tetrahydroborate (1.82 g, 48.21 mmol) and stir overnight. Quench the reaction mixture with ammonium hydroxide and filter the mixture. From the filtrate remove the solvent and extract the residue with dichloromethane, wash with saturated aqueous sodium chloride and dry over Na2SO4, filter and remove the solvent to obtain a dark yellow oil (4.2 g). MS (ES) m/z 157 [M+1]+.

Workup

  1. stirringstir overnight
  2. customQuench the reaction mixture with ammonium hydroxide
  3. filtrationfilter the mixture
  4. customFrom the filtrate remove the solvent
  5. extractionextract the residue with dichloromethane
  6. washwash with saturated aqueous sodium chloride
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customremove the solvent

Sources & evidence

ORD record
ord-43ddad6d5af44e18aea4a66ff2af4dde
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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