Aluminium lithium hydride → 2-(6-Chloropyridin-3-yl)ethan-1-amine

HRID 76147Notes

Reaction equation

HRID 76147 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=O)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 532788782-(6-Chloropyridin-3-YL)acetamide

Product 1

HCID 204834902-(6-Chloropyridin-3-yl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.00 g (11.7 mmol) 2-(6-chloropyridin-3-yl)-acetamide in 50 mL THF at 0° C. are added 12.9 ml LAH (c=1 mol/l in THF) by a dropping funnel. Cooling is removed and the reaction mixture is stirred for 1 h at r.t., then 8 ml LAH (c=1 mol/l in THF) are added and the reaction mixture is stirred at r.t. over night. The reaction is carefully quenched by the addition of 2 ml of an aq. NaHCO3 solution (10%). The mixture is filtrated and the solvent is removed under reduced pressure. The crude product is used without further purification.

Workup

  1. temperatureCooling
  2. customis removed
  3. addition8 ml LAH (c=1 mol/l in THF) are added
  4. stirringthe reaction mixture is stirred at r.t. over night
  5. customThe reaction is carefully quenched by the addition of 2 ml of an aq. NaHCO3 solution (10%)
  6. filtrationThe mixture is filtrated
  7. customthe solvent is removed under reduced pressure
  8. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-6fa8e2e68557410f80bfcc1187747a94
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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