methyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate → Methyl 2-amino-2-(pyridin-2-YL)acetate

HRID 1040458Notes

Reaction equation

HRID 1040458 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[N:11]O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1>C(O)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]([NH2:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 1

HCID 135778783methyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate

Product 1

HCID 10909919Methyl 2-amino-2-(pyridin-2-YL)acetateYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Hydroxyimino-pyridin-2-yl-acetic acid methyl ester (2.0 g, 11.1 mmol) in ethanol (50 mL) was placed in a round bottom flask. The flask was evacuated under vacuum and filled with Ar2 three times. Then 200 mg of 10% Pd on Carbon was added in one portion. The flask was evacuated again under vacuum and filled with Hydrogen three times. The reaction was stirred at room temperature under a balloon containing H2 for 16 h. The mixture was filtered through a pad of celite and rinsed with DCM three times. The combined organics were concentrated down to give Amino-pyridin-2-yl-acetic acid methyl ester (1.8 g) as a yellow oil which was used immediately in next step without further purification, m/z 167.55 [M+1]+

Workup

  1. customThe flask was evacuated under vacuum
  2. additionfilled with Ar2 three times
  3. additionThen 200 mg of 10% Pd on Carbon was added in one portion
  4. customThe flask was evacuated again under vacuum
  5. additionfilled with Hydrogen three times
  6. additioncontaining H2 for 16 h
  7. filtrationThe mixture was filtered through a pad of celite
  8. washrinsed with DCM three times
  9. concentrationThe combined organics were concentrated down

Sources & evidence

ORD record
ord-d9b3fd791f5b4000904278fb8e4059b2
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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