Boron tribromide → 8-bromo-5-hydroxy-4-(2-hydroxyethyl)quinolin-2(1H)-one

HRID 1627919Notes

Reaction equation

HRID 1627919 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16]C)=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[C:7]2[CH2:13][CH2:14][OH:15].B(Br)(Br)Br>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[C:7]2[CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 595785858-Bromo-4-(2-hydroxyethyl)-5-methoxyquinolin-2(1h)-one

Product 1

HCID 595786388-bromo-5-hydroxy-4-(2-hydroxyethyl)quinolin-2(1H)-oneYield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 8-bromo-4-(2-hydroxyethyl)-5-methoxyquinolin-2(1H)-one (2.7 g; 9.06 mmol) at −78° C. was added a solution of boron tribromide (1M in DCM) (55 ml; 55 mmol) dropwise. After 1 h the reaction mixture was allowed to warm up to room temperature and the stirring was carried out for 20 h. The reaction mixture was mixed with ice and water, the solid formed was isolated by filtration and dried over phosphorus pentoxide under reduced pressure to afford 1.56 g (45%) of 8-bromo-5-hydroxy-4-(2-hydroxyethyl)quinolin-2(1H)-one. The crude solid was used in the next step without further purification.

Workup

  1. waitthe stirring was carried out for 20 h
  2. customthe solid formed
  3. customwas isolated by filtration
  4. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-b2b795974a0c428281043e20865f29d1
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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