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

HRID 1701400Notes

Reaction equation

HRID 1701400 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(O[CH:13]=[C:14]([C:20]#[N:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C1(C)C=CC=CC=1.CCCCCC>[C:20]([C:14](=[CH:13][NH:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:21]

Participants

5

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 110516363-Ethylpyridin-2-amine

Product 1

HCID 70593218Ethyl 2-cyano-3-(3-ethyl-2-pyridylamino)acrylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of 2-amino-3-ethylpyridine (13.0 g., 0.1063 mole) and ethyl ethoxymethylenecyanoacetate (18.0 g., 0.1063 mole) in toluene (50 ml.) was heated on a steam bath for 20 minutes. The solution was cooled and the resulting mixture diluted with Skellysolve B. The title compound (19.0 g.), m.p. 122°-125° C., was collected by filtration. From the mother liquors, after recrystallization from cyclohexane, was obtained a further crop (7.0 g.) of product, m.p. 122°-125° C. Total yield of title compound, 26.0 g. (99.6%). The material from cyclohexane was recrystallized twice from methanol to give analytical material, m.p. 123°-125° C.

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe title compound (19.0 g.), m.p. 122°-125° C., was collected by filtration
  3. customFrom the mother liquors, after recrystallization from cyclohexane
  4. customwas obtained a further crop (7.0 g.) of product, m.p. 122°-125° C

Sources & evidence

ORD record
ord-fe5e2fc7a5854eb486793a326f927724
Source dataset
uspto-grants-1980_03
Patent number
US04192944

Reaction notes

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