Trifluoroacetic acid → Ethyl 2-(6-(methylamino)pyridin-2-yl)acetate

HRID 985482Notes

Reaction equation

HRID 985482 reaction equation
C(O[N:6]([C:10]1[N:15]=[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:12][CH:11]=1)[C:7](C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:7][NH:6][C:10]1[N:15]=[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22507075ethyl 2-{6-[(tert-butoxy)-N-methylcarbonylamino]-2-pyridyl}acetate

Product 1

HCID 22507068Ethyl 2-(6-(methylamino)pyridin-2-yl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-{6-[(tert-butoxy)-N-methylcarbonylamino]-2-pyridyl}acetate (3.56 g, 12.1 mmol) in dichloromethane (15 ml) was added trifluoroacetic acid (8 ml). The reaction was stirred for 16 h. The solvent was removed under vacuum and the crude product was chromatographed over silica gel to yield 2.2 g (100%) of Ethyl 2-[6-(methylamino)-2-pyridyl]acetate.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-fe756ca3d2c144cfbc76617fb511544d
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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