Ammonium Hydroxide → 1-(6-Chloropyridin-3-yl)ethan-1-amine

HRID 1640884Notes

Reaction equation

HRID 1640884 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][C:7]([C:10](=[N:12]O)[CH3:11])=[CH:6][CH:5]=1.[OH-].[NH4+]>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[Cl:3][C:4]1[N:9]=[CH:8][C:7]([CH:10]([NH2:12])[CH3:11])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 53396275HCID 53396275, compound

Product 1

HCID 157456051-(6-Chloropyridin-3-yl)ethan-1-amineYield 38.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Cool a solution of sodium borohydride (2.96 g, 82.65 mmol) and titanium tetrachloride (1 M in toluene, 41.33 mL, 41.33 mmol) in 50 mL of dry 1,2-dimethoxyethane to 0° C. under N2. Add 1-(6-chloropyridin-3-yl)ethanone oxime (3.52 g, 20.66 mmol) to the solution dropwise. Stir the mixture overnight at RT. Quench the reaction with 200 mL of water. Basify the mixture with ammonium hydroxide. Subsequently, extract the crude product into toluene and ethyl acetate. Separate the layers and dry the organic layer over sodium sulfate. Concentrate in vacuo to give the crude product (1.24 g, 38%). 1H NMR (400 MHz, CDCl3) δ 3.53 (s, 3H), 5.23 (s, 2H), 7.39 (d, J=4.0 Hz, 1H), 7.96 (d, J=1.6 Hz, 1H).

Workup

  1. customQuench
  2. customthe reaction with 200 mL of water
  3. extractionSubsequently, extract the crude product into toluene and ethyl acetate
  4. customSeparate the layers
  5. dry with materialdry the organic layer over sodium sulfate
  6. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-14f347a129674ea6a8d76699682436b9
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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