Ammonia → 5-(3,4-Dichlorobutyl)pyridine-2-carboxamide

HRID 1580974Notes

Reaction equation

HRID 1580974 reaction equation
[Cl:1][CH:2]([CH2:14][Cl:15])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](O)=[O:12])=[N:9][CH:10]=1.S(Cl)(Cl)=O.C(Cl)(Cl)Cl.[NH3:24]>C1C=CC=CC=1>[Cl:1][CH:2]([CH2:14][Cl:15])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH2:24])=[O:12])=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 2181975-(3,4-Dichlorobutyl)pyridine-2-carboxylic acid

Product 1

HCID 132718785-(3,4-Dichlorobutyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 g of 5-(3,4-dichlorobutyl)picolinic acid was added to the solution of thionyl chloride (30 ml) and chloroform (100 ml), and resulting solution was refluxed for fifteen minutes. The reaction mixture was evaporated in reduced pressure to obtain oily residue. This was dissolved in 100 ml of benzene and treated with 28% aqueous ammonia (50 ml) at 4° - 10°C with vigorous stirring for an hour. Benzene extract was evaporated in reduced pressure to give crude product as solid.

Workup

  1. customresulting solution
  2. temperaturewas refluxed for fifteen minutes
  3. customThe reaction mixture was evaporated in reduced pressure
  4. customto obtain oily residue
  5. extractionBenzene extract
  6. customwas evaporated in reduced pressure
  7. customto give crude product as solid

Sources & evidence

ORD record
ord-199681186ad64a948c28d562c5d279a8
Source dataset
uspto-grants-1976_01
Patent number
US03935221

Reaction notes

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