Pyridine → HCID 71117430, compound

HRID 2368529Notes

Reaction equation

HRID 2368529 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[CH3:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.N1C=CC=CC=1>ClCCl>[CH3:8][N:9]([CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 81436N-Methylpyridine-4-methylamine

Product 1

HCID 71117430HCID 71117430, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl chlorooxoacetate (2.01 g, 16.37 mmol), N-methyl-N-(4-pyridinylmethyl)amine (2.0 g, 16.37 mmol) and pyridine (1.6 mL, 19.64 mmol) in anhydrous dichloromethane (10 mL) was stirred at 50° C. for 2 h. The mixture was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (40%-100% EtOAc in hexanes) to afford methyl 2-(methyl(pyridin-4-ylmethyl)amino)-2-oxoacetate (77) as a pale yellow oil (0.96 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (40%-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-49cce757088242aa976e4df3c1ac02a6
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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