2-Aminopyridine → 2-Amino-1-(3-ethoxy-2,3-dioxopropyl)pyridin-1-ium bromide

HRID 860027Notes

Reaction equation

HRID 860027 reaction equation
[Br:1][CH2:2][C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>COCCOC>[Br-:1].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=1[CH2:2][C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 66144Ethyl bromopyruvate

Product 1

HCID 438112442-Amino-1-(3-ethoxy-2,3-dioxopropyl)pyridin-1-ium bromide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyl bromopyruvate (51.9 g, 266 mmol) was added dropwise to a solution of 2-aminopyridine (25 g, 266 mmol) in ethylene glycol dimethyl ether (270 mL), and the reaction then stirred at room temperature for 1 hour. The resulting precipitate was filtered off, the solid washed with ether and dried to afford the title compound as a pale yellow solid, 71.9 g.

Workup

  1. customthe reaction
  2. filtrationThe resulting precipitate was filtered off
  3. washthe solid washed with ether
  4. customdried

Sources & evidence

ORD record
ord-b367e844659c4f61bfd5205bdf54893f
Source dataset
uspto-grants-2006_12
Patent number
US07153870B2

Reaction notes

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