Hydrochloric Acid → 2-Chloro-3,3'-bipyridine

HRID 465112

Reaction equation

HRID 465112 reaction equation
CN(C)[CH:3]=[CH:4][CH:5]=[C:6]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:7]#[N:8].[ClH:16].C(=O)([O-])[O-].[K+].[K+].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C(O)(=O)C.C(OCC)(=O)C.CCCCCC>[Cl:16][C:10]1[C:9]([C:6]2[CH:7]=[N:8][CH:3]=[CH:4][CH:5]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66225Magnesium orthosilicateHCID 54400662alpha-[3-(Dimethylamino)-2-propenylidene]-3-pyridineacetonitrile

Product 1

HCID 104200582-Chloro-3,3'-bipyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

A 3.0 g portion of α-[3-(dimethylamino)-2-propenylidene]-3-pyridineacetonitrile was dissolved in 100 ml of glacial acetic acid. Dry hydrogen chloride gas (about 2.5 g) was introduced and the solution was heated at 60° C. for 3 hours. The reaction was cooled to 20° C. and then poured onto 200 g of ice. The solution was basified with potassium carbonate and then extracted with four 100 ml portions of methylene chloride. The organic extracts were combined, dried and the solvent removed at reduced pressure, giving an oil. This oil was dissolved in ethyl acetate:hexane (1:1) and passed through a pad of hydrous magnesium silicate. The solid obtained was recrystallized from hexane, giving 2-chloro-3,3'-bipyridine as white needles, mp 92°-93.5° C.

Workup

  1. temperatureThe reaction was cooled to 20° C.
  2. extractionextracted with four 100 ml portions of methylene chloride
  3. customdried
  4. customthe solvent removed at reduced pressure
  5. customgiving an oil
  6. customThe solid obtained
  7. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-0fcd7bd756e8416cb65495eaf1fc02fb
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Linked notes

Loading…