Sodium Cyanide → 2,8-Dimethyl-4-oxo-4H-1-benzopyran-5-carbonitrile

HRID 557430Notes

Reaction equation

HRID 557430 reaction equation
N[C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4](=[O:14])[CH:5]=[C:6]([CH3:13])[O:7]2.N([O-])=O.[Na+].C(=O)(O)[O-].[Na+].[Cu][C:25]#[N:26].[C-]#N.[Na+]>S(=O)(=O)(O)O.O.C(OCC)(=O)C>[CH3:13][C:6]1[O:7][C:8]2[C:9]([CH3:12])=[CH:10][CH:11]=[C:2]([C:25]#[N:26])[C:3]=2[C:4](=[O:14])[CH:5]=1

Participants

9

Reactant 5

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 57438891HCID 57438891, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 578286402,8-Dimethyl-4-oxo-4H-1-benzopyran-5-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.2 g (1.06 mmol) of 5-amino-2,8-dimethyl-4H-chromen-4-one is dissolved in 5 ml of 45% strength sulfuric acid and cooled to 0° C. A solution of 0.11 g (1.6 mmol) of sodium nitrite in 5 ml of water is then added dropwise in such a way that the temperature does not exceed 5° C. The mixture is stirred at 0° C. for 90 min and then neutralized with sodium bicarbonate. A solution of 0.12 g (1.37 mmol) of copper(I) cyanide and 0.07 g (1.58 mmol) of sodium cyanide in 10 ml of water, cooled to 0° C. and covered with a layer of 50 ml of ethyl acetate, is then added. The mixture is stirred at 0° C. for 45 min. The reaction mixture is then filtered through kieselguhr. The organic phase is separated off and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution. After drying over magnesium sulfate, the solvent is removed in vacuo. 0.14 g (67% of theory) of the title compound is obtained.

Workup

  1. customdoes not exceed 5° C
  2. additionis then added
  3. stirringThe mixture is stirred at 0° C. for 45 min
  4. filtrationThe reaction mixture is then filtered through kieselguhr
  5. customThe organic phase is separated off
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. washThe combined organic phases are washed with saturated sodium chloride solution
  8. dry with materialAfter drying over magnesium sulfate
  9. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-322a558c7a4144aeb66419f24d587439
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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