Sodium Cyanide → HCID 19735104, compound

HRID 326590Notes

Reaction equation

HRID 326590 reaction equation
Br[C:2]1[C:3]([CH3:20])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.[C-:21]#[N:22].[Na+]>CN(C)C=O.O>[C:21]([C:2]1[C:3]([CH3:20])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1)#[N:22]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 10640221HCID 10640221, compound

Product 1

HCID 19735104HCID 19735104, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cuprous cyanide (1.1 g) was added to a solution of Compound 46 (2.0 g) in dimethylformamide (5 ml) and the mixture was heated under reflux for 23 hours. The reaction mixture was air-cooled. The mixture was then added to a solution of sodium cyanide (2.2 g) in water (6.5 ml), and the mixture was stirred for 15 minutes. The mixture was extracted with ethyl acetate, successively washed with aqueous 5% sodium cyanide solution and saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off. The resulting crude product was washed with ether/isopropyl ether to obtain 6-cyano-2,2,7-trimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.35 g) (Compound 64).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 23 hours
  3. temperatureThe reaction mixture was air-cooled
  4. extractionThe mixture was extracted with ethyl acetate
  5. washsuccessively washed with aqueous 5% sodium cyanide solution and saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. washThe resulting crude product was washed with ether/isopropyl ether

Sources & evidence

ORD record
ord-f815011882004ae98d963dcbe256d7ef
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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