Dimethylformamide → HCID 20563052, compound

HRID 127354

Reaction equation

HRID 127354 reaction equation
N[C:2]1[O:3][C:4]2[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=2[C:6](=[O:10])[C:7]=1C=O.[C:15]([C:17]#[CH:18])#[N:16].[CH3:19][N:20](C)C=O>>[C:15]([C:17]1[CH:19]=[N:20][C:7]2[C:6](=[O:10])[C:5]3[C:4]([O:3][C:2]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)#[N:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 140552-PropynenitrileHCID 7359282-Aminochromone-3-carboxaldehyde

Product 1

HCID 20563052HCID 20563052, compound

Conditions

Temperature
140 °C

Procedure

To 70 ml of dimethylformamide was added 2.2 g of 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehyde, followed by the addition of 2.5 g of cyanoacetylene. The mixture was heated under stirring at 140° C. for 15 hours and the solvent was then distilled off under reduced pressure. The residue was chromatographed on silica gel and eluted with chloroform and recrystallized from acetonitrile to give 0.83 g of 3-cyano-1-azaxanthone as crystals, m.p. 220°-226° C.

Workup

  1. temperatureThe mixture was heated
  2. distillationthe solvent was then distilled off under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluted with chloroform
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-1024b56898ab4dc3a52291c2bd63f8af
Source dataset
uspto-grants-1981_03
Patent number
US04255576

Linked notes

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