Dimethylformamide → HCID 20563001, compound

HRID 127352Notes

Reaction equation

HRID 127352 reaction equation
N[C:2]1[O:3][C:4]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][C:5]=2[C:6](=[O:10])[C:7]=1C=O.[C:17]([CH2:19][C:20](Cl)=O)#[N:18].C[N:24]([CH3:27])C=O>>[CH2:15]([C:12]1[CH:11]=[C:5]2[C:4]([O:3][C:2]3[CH:20]=[C:19]([C:27]#[N:24])[CH:17]=[N:18][C:7]=3[C:6]2=[O:10])=[CH:14][CH:13]=1)[CH3:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 110515942-Cyanoacetyl chlorideHCID 126892482-Amino-6-ethyl-4-oxo-4H-1-benzopyran-3-carbaldehyde

Product 1

HCID 20563001HCID 20563001, compound

Procedure

In 40 ml of dimethylformamide was dissolved 1.82 g of 2-amino-6-ethyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde, followed by the addition of 3.5 g of cyanoacetyl chloride. The mixture was reacted at 60° C. for 3 hours, with constant stirring. The solvent was then distilled off under reduced pressure and the residue was chromatographed on silica gel. The desired product was recovered from the chloroform eluate and recrystallized from acetonitrile. By the above procedure was obtained 1.03 g of 7-ethyl-3-cyano-1-azaxanthone, m.p. 183°-185° C.

Workup

  1. customThe mixture was reacted at 60° C. for 3 hours, with constant stirring
  2. distillationThe solvent was then distilled off under reduced pressure
  3. customthe residue was chromatographed on silica gel
  4. customThe desired product was recovered from the chloroform eluate
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-a911142a138e4bff8d6eef07c1415a56
Source dataset
uspto-grants-1981_03
Patent number
US04255576

Reaction notes

Loading…