Ethyl Acetate → Methanone, (6-chloro-3-pyridinyl)phenyl-

HRID 277919Notes

Reaction equation

HRID 277919 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][N:7]=1.CCO[C:18]([CH3:20])=O.[OH-].[Na+]>C1C=CC=CC=1>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](=[O:11])[C:20]2[CH:18]=[CH:14][CH:13]=[CH:9][CH:8]=2)=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 27821656-Chloronicotinoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3061713Methanone, (6-chloro-3-pyridinyl)phenyl-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Aluminum chloride (100 g, 0.730 mol) was suspended in 200 ml benzene under N2. A solution of 6-chloronicotinoyl chloride (53 g, 0.30 mol) in 100 ml benzene was added to the rapidly stirring suspension then refluxed overnight. The reaction was cooled to RT, 1 L EtOAc was added, and the pH was adjusted to 8.5 with 5N NaOH. Aluminum salts precipitated and were filtered away. The filtrate was washed with H2O, dried over Na2SO4, and concentrated in vacuo. The resulting tan solid was recrystallized from 3:2 Et2O:hexanes yielding 54.6 g (83%) of product as tan crystals. EA, MS(FD).

Workup

  1. temperaturethen refluxed overnight
  2. customAluminum salts precipitated
  3. filtrationwere filtered away
  4. washThe filtrate was washed with H2O
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting tan solid was recrystallized from 3:2 Et2O

Sources & evidence

ORD record
ord-46294cc4e21e46c697ae583ef0f5b5b9
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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