Diethyl Ether → N-cyanomethyl-2-chloroisonicotinamide

HRID 1381985Notes

Reaction equation

HRID 1381985 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[NH2:8][CH2:9][C:10]#[N:11].[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][N:21]=1)[C:16](Cl)=[O:17].CCOCC>O.C(OCC)(=O)C>[C:10]([CH2:9][NH:8][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][N:21]=[C:13]([Cl:12])[CH:14]=1)#[N:11]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 196971Aminoacetonitrile sulfate (1:1)HCID 28000032-Chloropyridine-4-carbonyl chloride

Product 1

HCID 14054581N-cyanomethyl-2-chloroisonicotinamideYield 81.2%

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 and the mixture was stirred at room temperature for 1 h and then cooled to 5° C. or below. A liquid mixture of 3.0 g (0.017 mol) of 2-chloroisonicotinoyl chloride and 30 ml of ether was added dropwise thereto at 5° C. or below lest unfavorable heat generation should occur. The mixture was then stirred at room temperature for 2 h to conduct a reaction. Water and ethyl acetate were added thereto to conduct extraction. The extract was washed with a saturated aqueous common salt solution, dried over anhydrous sodium sulfate and concentrated. The resulting crystals were recrystallized from a liquid mixture of n-hexane and ethyl acetate to obtain 2.7 g (yield: 81.2%) of the intended product as white crystals having a melting point of 131° to 132° C.

Workup

  1. temperaturecooled to 5° C. or below
  2. additionwas added dropwise
  3. customat 5° C. or below
  4. stirringThe mixture was then stirred at room temperature for 2 h
  5. customa reaction
  6. extractionextraction
  7. washThe extract was washed with a saturated aqueous common salt solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe resulting crystals were recrystallized from a liquid mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-84880bc6d7f541aeb60720a6915b07e0
Source dataset
uspto-grants-1989_02
Patent number
US04804762

Reaction notes

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