Methanol → HCID 22417838, compound

HRID 1720274Notes

Reaction equation

HRID 1720274 reaction equation
B(Br)(Br)[Br:2].[Cl:5][C:6]1[C:15]2[C:10](=[C:11](OC)[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][CH:7]=1.C[OH:19]>ClCCl>[BrH:2].[Cl:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=2)[N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 123366624-Chloro-8-methoxyquinoline

Product 1

HCID 22417838HCID 22417838, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a flame dried three-neck 50 mL round bottom flask equipped with a rubber septum and a mechanical stirrer, and under a nitrogen atmosphere at room temperature, 4.0 mL of 1.0M boron tribromide in dichloromethane (Aldrich Chemical Co.) was added portionwise through gas tight syringe to a solution of 727 mg (3.75 mmol) of 4-chloro-8-methoxyquinoline and 5.0 mL of dichloromethane. A thick solid formed immediately and after 0.5 hour of stirring another 4.0 mL portion of boron tribromide solution was added and stirring was continued overnight. The reaction mixture was treated dropwise with methanol. The solution was evaporated under reduced pressure, and the residue titurated with dichloromethane and filtered to afford 844 mg (86%) of the title compound: m.p. 243°-244° C.

Workup

  1. customIn a flame dried three-neck 50 mL round bottom flask
  2. customequipped with a rubber septum and a mechanical stirrer
  3. customA thick solid formed immediately and after 0.5 hour
  4. additionwas added
  5. customThe solution was evaporated under reduced pressure
  6. filtrationfiltered

Sources & evidence

ORD record
ord-80b5d41f28d04303b08e17a5b9eb2a32
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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