Aluminum(III) Chloride → HCID 58294438, compound

HRID 521013Notes

Reaction equation

HRID 521013 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[C:14]([C:19](Cl)=[O:20])=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:10]=[CH:11][CH:12]=1>ClCCl>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]2[C:19](=[O:20])[C:14]3[C:13]([C:9]=2[CH:8]=1)=[CH:18][CH:17]=[CH:16][N:15]=3

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 58294393HCID 58294393, compound

Product 1

HCID 58294438HCID 58294438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (7.33 g) is added to a solution of 3-(3-methoxy-phenyl)-pyridine-2-carbonyl chloride (crude, 5.40 g) in dichloromethane (100 mL) chilled in an ice bath. The cooling bath is removed and the mixture is stirred at room temperature overnight. The mixture is then poured on crushed ice and the resulting mixture is extracted with dichloromethane. The combined extracts are washed with aqueous NaHCO3 solution and dried (Na2SO4). The solvent is evaporated and the residue is triturated with a mixture of cyclohexane and ethyl acetate (1:1) and dried to give the title compound as a yellowish solid. Yield: 3.00 g (65% of theory); LC (method 1): tR=2.84 min; Mass spectrum (ESI+): m/z=212 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionThe mixture is then poured
  4. customon crushed ice
  5. extractionthe resulting mixture is extracted with dichloromethane
  6. washThe combined extracts are washed with aqueous NaHCO3 solution
  7. dry with materialdried (Na2SO4)
  8. customThe solvent is evaporated
  9. customthe residue is triturated with a mixture of cyclohexane and ethyl acetate (1:1)
  10. customdried

Sources & evidence

ORD record
ord-fbda81223714452fa83ed663daae808c
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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