Diethyl (ethoxymethylene)malonate → HCID 22397139, compound

HRID 1070640Notes

Reaction equation

HRID 1070640 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=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>>[Cl:1][C:2]1[C:7]([NH:8][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 27344153-Amino-2-chloro-6-picoline

Product 1

HCID 22397139HCID 22397139, compoundYield 95%

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-6-methyl-3-pyridinylamine (8.5 g) and diethyl ethoxymethylenemalonate (22.0 mL) is heated at 140° C. for 18 hours. The mixture is cooled to room temperature and the resulting solids are recrystallized from a mixture of heptane (400 mL) and CH2Cl2 (2 mL) to obtain 17.9 g (95%) of the title compound as a pale red solid. Physical characteristics: MS (ESI+) m/z 313 (M+H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customthe resulting solids are recrystallized from a mixture of heptane (400 mL) and CH2Cl2 (2 mL)

Sources & evidence

ORD record
ord-8f9a672be492464d9e6d1e8f7ae1c63f
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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