Boron tribromide → HCID 10976036, compound

HRID 504002Notes

Reaction equation

HRID 504002 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:8]=1[CH2:9][CH2:10][C:11](=[O:18])[NH:12]2>ClCCl>[OH:6][C:7]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:8]=1[CH2:9][CH2:10][C:11](=[O:18])[NH:12]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66597026HCID 66597026, compound

Product 1

HCID 10976036HCID 10976036, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2N dichloromethane solution (52 ml) of boron tribromide was added dropwise at −20° C. to a dichloromethane solution (100 ml) of 5-methoxy-8-methyl-3,4-dihydro-1H-quinolin-2-one (10.0 g). After stirring for 1 hour, the reaction mixture was poured into ice water and separated into layers. The organic layer was washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from an ethyl acetate-diethyl ether mixed solvent to thereby obtain 9.4 g (yield: quantitative) of 5-hydroxy-8-methyl-3,4-dihydro-1H-quinolin-2-one as a white powder.

Workup

  1. customseparated into layers
  2. washThe organic layer was washed twice with water
  3. washwashed with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from an ethyl acetate-diethyl ether mixed solvent

Sources & evidence

ORD record
ord-0f90844cf5a4483eb02818e12ef538d9
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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