Aluminium lithium hydride → 2-[6-(Methylamino)-2-pyridyl]ethan-1-ol

HRID 985483Notes

Reaction equation

HRID 985483 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][C:10](OCC)=[O:11])[CH:6]=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22507068Ethyl 2-(6-(methylamino)pyridin-2-yl)acetate

Product 1

HCID 105348582-[6-(Methylamino)-2-pyridyl]ethan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-[6-(methylamino)-2-pyridyl]acetate (2.2 g, 12.5 mmol) in THF (30 ml) was added dropwise to a suspension of lithium aluminum hydride (1.24 g, 31.2 mmol) in TEF (25 ml) under argon at 0° C. The reaction was stirred for 30 minutes and quenched carefully with water (4 ml) and 1 N NaOH (4 ml). The mixture was filtered through a pad of Celite and washed several times with ethyl acetate. The filtrate was dried with sodium sulfate, filtered, and evaporated under vacuum. The crude product was chromatographed over silica gel to yield 1.50 g (79%) of 2-[6-(Methylamino)-2-pyridyl]ethan-1-ol.

Workup

  1. customquenched carefully with water (4 ml) and 1 N NaOH (4 ml)
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washwashed several times with ethyl acetate
  4. dry with materialThe filtrate was dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-2cb37485fee340708b049a3e0fb6e981
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

Loading…