3-Aminopyridine → Ethyl 2-cyano-3-(pyridin-3-ylamino)acrylate

HRID 869445Notes

Reaction equation

HRID 869445 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[C:8](/[C:10](=[CH:16]\OCC)/[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9]>C1(C)C=CC=CC=1>[C:8]([C:10](=[CH:16][NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9]

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 1715183Ethyl 2-cyano-3-ethoxyacrylate

Product 1

HCID 71226778Ethyl 2-cyano-3-(pyridin-3-ylamino)acrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of pyridin-3-amine (C-1) (10.0 g, 106.3 mmol, 1.0 eq) and (E)-ethyl 2-cyano-3-ethoxyacrylate (C-2) (21.5 g, 127 mmol, 1.2 eq) in toluene (40 mL) is stirred at reflux under argon for 5 h and then allowed to cool to RT. The precipitate is collected by filtration, rinsed with a mixture of petroether and ethyl acetate (v/v=2:1, 3×10 mL), and then dried in vacuo to afford the product, ethyl 2-cyano-3-(pyridin-3-ylamino)acrylate (C-3).

Workup

  1. temperatureat reflux under argon for 5 h
  2. filtrationThe precipitate is collected by filtration
  3. washrinsed with a mixture of petroether and ethyl acetate (v/v=2:1, 3×10 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3b1dd2a6af12464b994ad6d06c885d6d
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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