3-Cyanopyridine → HCID 12218259, compound

HRID 617645Notes

Reaction equation

HRID 617645 reaction equation
[CH2:1]([OH:3])[CH3:2].C([Cl:7])(=O)C.[C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)#[N:9]>C(Cl)(Cl)Cl>[ClH:7].[ClH:7].[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:8](=[NH:9])[O:3][CH2:1][CH3:2])[CH:11]=1

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 702EthanolHCID 6367Acetyl chloride

Product 1

HCID 12218259HCID 12218259, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of chloroform (100 mL) and ethanol (200 mL) was added dropwise acetyl chloride (190 mL, 2.67 mol) under ice-cooling over 1 h. The resulting solution was stirred at oec for 30 min, whereafter a solution of 3-cyanopyridine (25.5 g, 245 mmol) in chloroform (300 mL) was added dropwise over 1.5 h. After stirring at room temperature for 17 h, precipitates were collected by filtration, washed with chloroform, and dried in vacuo to give 50.5 g (92%) of ethyl 3-pyridinecarboximidate dihydrochloride as colorless crystals.

Workup

  1. temperaturecooling over 1 h
  2. stirringAfter stirring at room temperature for 17 h
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. washwashed with chloroform
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8c47ebf1e26b4c00a731e1008a157bf3
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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