Potassium Carbonate → 6-Amino-2-pyridinemethanol

HRID 861979Notes

Reaction equation

HRID 861979 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]([NH:9]C(=O)C(C)(C)C)[CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=[O:17].[K+].[K+]>OS(O)(=O)=O>[NH2:9][C:7]1[N:8]=[C:3]([CH2:2][OH:17])[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14326706N-[6-(Bromomethyl)pyridin-2-yl]-2,2-dimethylpropanamide

Product 1

HCID 111826066-Amino-2-pyridinemethanolYield 71%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The product of Example 2 (24.89 g, 96 mmol) and 10% (v/v) H2SO4 (100 mL) were combined in a 250 mL flask. The reaction was heated to reflux for 8 h and then cooled to room temperature. The reaction was made basic with aq K2CO3 and extracted with EtOAc. The extracts were dried (MgSO4), decolorized with activated charcoal, and filtered. Removal of all solvent in vacuo gave 8.49 g (71%) of the desired product.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 8 h
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customRemoval of all solvent in vacuo

Sources & evidence

ORD record
ord-426534e4e3a345d9a21b2e71ae533e8f
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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