Boron tribromide → HCID 18317642, compound

HRID 1700754Notes

Reaction equation

HRID 1700754 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:24]C)=[C:10]([CH:12]2[CH2:21][C:20]3[N:19]=[CH:18][CH:17]=[C:16]([CH3:22])[C:15]=3[C:14](=[O:23])[CH2:13]2)[CH:11]=1.C(=O)([O-])O.[Na+]>ClCCl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:24])=[C:10]([CH:12]2[CH2:21][C:20]3[N:19]=[CH:18][CH:17]=[C:16]([CH3:22])[C:15]=3[C:14](=[O:23])[CH2:13]2)[CH:11]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 18317575HCID 18317575, compound

Product 1

HCID 18317642HCID 18317642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1M boron tribromide in dichloromethane (12.3 ml) was added dropwise a solution of 7-(5-chloro-2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.2 g) in dichloromethane (30 ml) at 0° C. The reaction solution was stirred at room temperature for 1.5 hours, and to the solution were added ice and sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with sodium sulfate. Under reduced pressure, the solvent was evaporated to give 7-(5-chloro-2-hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried with sodium sulfate
  4. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-54681edb3f58446989c15ee7953e5bde
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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