Diethyl (ethoxymethylene)malonate → Diethyl 2-(((6-methoxypyridin-3-yl)amino)methylene)malonate

HRID 2356306Notes

Reaction equation

HRID 2356306 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>CCO>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[CH:13][NH:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:19]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 619151Diethyl 2-(((6-methoxypyridin-3-yl)amino)methylene)malonateYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-amino-2-methoxypyridine (Aldrich, 100 g, 0.806 mole) and diethyl ethoxymethylenemalonate (Aldrich, 163 mL, 0.806 mole) in EtOH (1 L) was heated at reflux for 4 h, then was cooled to RT. Concentration to dryness gave the title compound (238 g, quantitative).

Workup

  1. temperatureat reflux for 4 h
  2. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-33c52e62b77e4351a56536b8dc1d01f8
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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