Cyanoacetic acid → HCID 2799775, compound

HRID 1903099Notes

Reaction equation

HRID 1903099 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:1]([CH2:3][C:4]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 195092-Pyridinemethanamine

Product 1

HCID 2799775HCID 2799775, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a solution of 6.8 g of cyanoacetic acid in 200 ml of acetonitrile was added a solution of 8.65 g of 2-aminomethylpyridine in 50 ml of acetonitrile, and to the resulting suspension there was added rapidly (with stirring) a solution of 18.5 g of dicyclohexylcarbodiimide in 50 ml of acetonitrile. After stirring 5 hours and standing overnight, the suspension was filtered. The filtrate was evaporated, and the crude residue was triturated with ether-ethyl acetate to give crystals, m.p. 78°-80°. Recrystallization from toluene yielded the 2-(cyanoacetylaminomethyl)-pyridine, m.p. 81°-82°.

Workup

  1. additionto the resulting suspension there was added rapidly
  2. waitstanding overnight
  3. filtrationthe suspension was filtered
  4. customThe filtrate was evaporated
  5. customthe crude residue was triturated with ether-ethyl acetate
  6. customto give crystals, m.p. 78°-80°
  7. customRecrystallization from toluene

Sources & evidence

ORD record
ord-f61fb57231064762a9e1ef3c7a1b6bf2
Source dataset
uspto-grants-1984_03
Patent number
US04435407

Reaction notes

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