Ethyl Acetate → (2-Aminopyridin-3-yl)methanol

HRID 2079998Notes

Reaction equation

HRID 2079998 reaction equation
[CH:1]([C:3]1[C:4]([NH:9]C(=O)C(C)(C)C)=[N:5][CH:6]=[CH:7][CH:8]=1)=[O:2].[OH-].[Na+].C(OCC)(=O)C>O1CCCC1>[NH2:9][C:4]1[C:3]([CH2:1][OH:2])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 736837N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamide

Product 1

HCID 11159325(2-Aminopyridin-3-yl)methanolYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture solution of N-(3-formylpyridin-2-yl)-2,2-dimethylpropionamide described in Preparation Example J-2 (500 mg, 2.4 mmol) and an aqueous solution of 5N sodium hydroxide (7 mL) was refluxed for 90 minutes. After cooling, ethyl acetate and tetrahydrofuran were added for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:5), and the title compound (160 mg, 1.2 mmol, 53%) was obtained as a pale yellow solid.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed with brine
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:5)

Sources & evidence

ORD record
ord-ea247e4cba964de2aaf81237f090b920
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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