2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → Ethyl 2-cyano-3-(5-phenyl-2-pyridylamino)acrylate

HRID 1701404Notes

Reaction equation

HRID 1701404 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1.C(O[CH:17]=[C:18]([C:24]#[N:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>>[C:24]([C:18](=[CH:17][NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:25]

Participants

3

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 1050975-Phenyl-2-pyridinamine

Product 1

HCID 70592147Ethyl 2-cyano-3-(5-phenyl-2-pyridylamino)acrylateYield 63.4%

Procedure

A mixture of 2-amino-5-phenylpyridine (1.19 g., 6.99 mmoles) and ethyl ethoxymethylenecyanoacetate (1.18 g., 6.99 mmoles) was fused at an oil bath temperature of 100° for 15 minutes. The product was recrystallized from toluene to give the title compound (1.3 g.), m.p. 126°-134°. An additional crop of product (0.3 g.), m.p. 119°-126° was obtained from the mother liquors. Total yield of product, 1.6 g. (78%).

Workup

  1. customwas fused at an oil bath
  2. customThe product was recrystallized from toluene

Sources & evidence

ORD record
ord-9905302041f74389b458e968266f8166
Source dataset
uspto-grants-1980_03
Patent number
US04192944

Reaction notes

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