Dimethylformamide → HCID 20253636, compound

HRID 638208Notes

Reaction equation

HRID 638208 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12](=[O:18])[NH:13]3)=[CH:4][CH:3]=1.[CH3:19][N:20](C)C=O>>[C:19]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12](=[O:18])[NH:13]3)=[CH:4][CH:3]=1)#[N:20]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 15696721HCID 15696721, compound

Product 1

HCID 20253636HCID 20253636, compound

Procedure

A mixture containing 15 g of 5-(4-bromophenyl)-1,6-naphthyridin-2(1H)-one, 300 ml of dimethylformamide and 8.6 g of cuprous cyanide was refluxed with stirring for 96 hours, cooled and stripped to dryness using a rotary evaporator. To the residue was added 300 ml of concentrated aqueous ammonium hydroxide solution and 20 ml of glacial acidic acid. The resulting mixture was chilled in ice, next treated with 71 ml of (5.25% aqueous sodium hypochlorite solution, then stirred in an ice bath for 3 hours and allowed to stand at room temperature for 4 hours. The brown solid was collected, washed with water, dried, dissolved in 300 ml of boiling dimethylformamide, the hot solution treated with decolorizing charcoal and filtered, and the filtrate concentrated to dryness. The residue was recrystallized from dimethylformamide to produce 8.6 g of 5-(4-cyanophenyl)-1,6-naphthyridin-2(1H)-one, m.p. >300° C.

Workup

  1. temperaturewas refluxed
  2. temperaturecooled
  3. customa rotary evaporator
  4. additionTo the residue was added 300 ml of concentrated aqueous ammonium hydroxide solution and 20 ml of glacial acidic acid
  5. temperatureThe resulting mixture was chilled in ice
  6. additionnext treated with 71 ml of (5.25% aqueous sodium hypochlorite solution
  7. stirringstirred in an ice bath for 3 hours
  8. waitto stand at room temperature for 4 hours
  9. customThe brown solid was collected
  10. washwashed with water
  11. customdried
  12. dissolutiondissolved in 300 ml of boiling dimethylformamide
  13. additionthe hot solution treated with decolorizing charcoal
  14. filtrationfiltered
  15. concentrationthe filtrate concentrated to dryness
  16. customThe residue was recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-e2493b0829784e279146481bc4725e4a
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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