Sodium ethoxide → HCID 18507515, compound

HRID 1356021Notes

Reaction equation

HRID 1356021 reaction equation
[NH2:1][C:2]([C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)=[C:3]([C:6](=[O:10])[CH2:7][C:8]#[N:9])[C:4]#[N:5].CC[O-].[Na+]>C(O)C>[NH2:9][C:8]1[NH:1][C:2]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[C:3]([C:4]#[N:5])[C:6](=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 69786726HCID 69786726, compound

Product 1

HCID 18507515HCID 18507515, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Following the method of Toledo et al. (Chem. Mater. 1994, 6, 1222), to a stirred solution 2.61 g (13.0 mmol) (E or Z)-2-(amino-furan-2-yl-methylene)-3-oxo-pentanedinitrile in 30 ml dry ethanol under argon at room temperature was added 4.86 ml (13.0 mmol) sodium ethylate solution (2.67M in ethanol) and the reaction mixture heated at 100° C. for 1 hour. The reaction mixture was then concentrated in vacuo and the residue dissolved in a minimum of water and acidified to pH 4.5 with glacial acetic acid. The resulting crystals were collected by filtration and washed sequentially with water and ether to afford 2,41 g (93%) 6-amino-2-furan-2-yl-4-oxo-1,4-dihydro-pyridine-3-carbonitrile as a white crystalline solid. ES-MS m/e (%): 200 ([M—H]−, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe residue dissolved in a minimum of water
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed sequentially with water and ether

Sources & evidence

ORD record
ord-96c1af2b8e84496fb1c8aa1face075ed
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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