2-Amino-5-methylpyridine → Ethyl 2-cyano-3-(5-methyl-2-pyridylamino)acrylate

HRID 1701401Notes

Reaction equation

HRID 1701401 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C(O[CH:12]=[C:13]([C:19]#[N:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[C:19]([C:13](=[CH:12][NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:20]

Participants

3

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 4480416Ethyl 2-cyano-3-(5-methyl-2-pyridylamino)acrylateYield 50.5%

Procedure

A mixture of 2-amino-5-methylpyridine (5.0 g., 46.2 mmoles) and ethyl ethoxymethylenecyanoacetate (7.82 g., 46.2 mmoles) was heated by means of an oil bath maintained at 100° for 15 minutes. The mixture was cooled and the resultant solid recrystallized from acetonitrile to give the title compound (5.4 g., 50.5%), m.p. 170°-171.5°.

Workup

  1. temperaturewas heated by means of an oil bath
  2. temperaturemaintained at 100° for 15 minutes
  3. temperatureThe mixture was cooled
  4. customthe resultant solid recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2459600189f240dbaeb4338248f38bef
Source dataset
uspto-grants-1980_03
Patent number
US04192944

Reaction notes

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