Ethanol → 1-(2-Aminopyridin-4-yl)ethanol

HRID 1845866Notes

Reaction equation

HRID 1845866 reaction equation
N([C:3]1[N:8]=[C:7]([CH:9]([OH:11])[CH3:10])[CH:6]=[CH:5][N:4]=1)N.[CH2:12](O)C>CO.[Ni]>[NH2:8][C:3]1[CH:12]=[C:7]([CH:9]([OH:11])[CH3:10])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 672565471-(2-Hydrazinopyrimidin-4-yl)ethanol

Product 1

HCID 179991481-(2-Aminopyridin-4-yl)ethanol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-(2-hydrazinopyrimidin-4-yl)ethanol (13a) was dissolved in ethanol (300 mL) and Raney-Ni (35 mL, 50% slurry in water) was added. The flask was flushed with argon, put under a hydrogen atmosphere (balloon) and stirred at room temperature overnight. The mixture was filtered and concentrated under vacuum to give a red oil that was dissolved in methanol and concentrated onto silica before being purified by silica flash chromatography (100% ethyl acetate to 20% methanol in ethyl acetate) to give the title compound (9.0 g) as an orange oil.

Workup

  1. customThe flask was flushed with argon
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under vacuum
  4. customto give a red oil that
  5. concentrationconcentrated onto silica
  6. custombefore being purified by silica flash chromatography (100% ethyl acetate to 20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-e95419049608414fa222b2aac96e5390
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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