Diethyl Ether → N-(cyanomethyl)-2-fluoroisonicotinamide

HRID 1381983Notes

Reaction equation

HRID 1381983 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[NH2:8][CH2:9][C:10]#[N:11].CCOCC.[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][N:26]=1)[C:21](Cl)=[O:22]>O.C(OCC)(=O)C>[C:10]([CH2:9][NH:8][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][N:26]=[C:18]([F:17])[CH:19]=1)#[N:11]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 196971Aminoacetonitrile sulfate (1:1)HCID 143034342-Fluoro-isonicotinoyl chloride

Product 1

HCID 14303435N-(cyanomethyl)-2-fluoroisonicotinamideYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2.4 g (0.056 mol) of sodium hydroxide was dissolved in 24 ml of water. 3.6 g (0.017 mol) of aminoacetonitrile sulfate was added to the solution. 30 ml of ether containing 3.0 g (0.017 mol) of 2-fluoroisonicotinoyl chloride was added dropwise to the solution while the temperature was kept below 5° C. The mixture was stirred at room temperature for 2 h to conduct a reaction. Water and ethyl acetate were added to the mixture to conduct extraction. The organic layer was washed with a saturated aqueous common salt solution and dried over anhydrous sodium sulfate. The solvent was distilled. The resulting crude crystalls were recrystallized from a solvent mixture of n-hexane and ethyl acetate to obtain 2.3 g (yield: 75.3%) of white crystal having a melting point of 124° to 125° C.

Workup

  1. customwas kept below 5° C
  2. customa reaction
  3. extractionextraction
  4. washThe organic layer was washed with a saturated aqueous common salt solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled
  7. customThe resulting crude crystalls were recrystallized from a solvent mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-43a5e0c544ad4db1b9a6d6364204dcfc
Source dataset
uspto-grants-1989_02
Patent number
US04804762

Reaction notes

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