Sodium Cyanide → HCID 18187277, compound

HRID 1357652Notes

Reaction equation

HRID 1357652 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[C:13]2[CH:16]([F:18])[F:17])[CH:11]=[CH:10][CH:9]=[N:8]3)=[CH:4][CH:3]=1.[C-:19]#[N:20].[Na+].CCOC(C)=O.CCCCCC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([C:19]#[N:20])([CH:16]([F:18])[F:17])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 18187295HCID 18187295, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18187277HCID 18187277, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method KKK To a stirred solution of 7-chloro-9-(difluoromethyl)-4-azaacridine (91) (1.28 g, 4.84 mmol) in anhydrous DMF (30 mL) at room temperature was added NaCN (711 mg, 14.51 mmol). After 15 h at room temperature, the reaction was quenched with H2O (150 mL), and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Flash chromatography (SiO2, 30% EtOAc-hexane) furnished 92 (747 mg, 53% yield) as a brown solid.

Workup

  1. customthe reaction was quenched with H2O (150 mL)
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75f726cd8b784d51ac054be262cd5d7d
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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