Cyanoacetic acid → 2-Cyano-N-(pyridin-2-yl)acetamide

HRID 1903096Notes

Reaction equation

HRID 1903096 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:1]([CH2:3][C:4]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 104392-AminopyridineHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 7061872-Cyano-N-(pyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cyanoacetic acid (4.5 g) and 5.0 g of 2-aminopyridine, each in acetonitrile, were combined, and the suspension (150 ml) treated rapidly with a solution of 12.0 g of dicyclohexylcarbodiimide (DCCI) in 60 ml of acetonitrile. After stirring 4 hrs. and filtering, the filtrate was evaporated and the residue triturated with ether to give 2-(cyanoacetylamino)pyridine, m.p. 159°-161°. Recrystallization from ethyl acetate raised melting point to 162°-3°.

Workup

  1. filtrationand filtering
  2. customthe filtrate was evaporated
  3. customthe residue triturated with ether

Sources & evidence

ORD record
ord-fff6fe8e91d342e0b8874e12322f778b
Source dataset
uspto-grants-1984_03
Patent number
US04435407

Reaction notes

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