Ethyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate → Ethyl 2-amino-2-(pyridin-2-yl)acetate

HRID 1867620Notes

Reaction equation

HRID 1867620 reaction equation
O/[N:2]=[C:3](/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5]>[Pd].C(O)C>[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 135741730Ethyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate

Product 1

HCID 4570669Ethyl 2-amino-2-(pyridin-2-yl)acetateYield 103.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (100 mg) was added to a solution of ethyl (2Z)-(hydroxyimino)(pyridin-2-yl)ethanoate (592 mg, 2.67 mmol) in ethanol (20 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 3 h, the mixture was filtered and concentrated to give the title compound (500 mg). MS 181.17 (M+1)

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e7df7e0c8e94120bc47e77f34259a8b
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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