Borane → 8-Bromo-4-(2-hydroxyethyl)-5-methoxyquinolin-2(1h)-one

HRID 1627918Notes

Reaction equation

HRID 1627918 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[C:7]2[CH2:13][C:14](O)=[O:15].B>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[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 6331BoraneHCID 595785222-(8-Bromo-5-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acetic acid

Product 1

HCID 595785858-Bromo-4-(2-hydroxyethyl)-5-methoxyquinolin-2(1h)-oneYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well-stirred and cold solution of 2-(8-bromo-5-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acetic acid (5.5 g; 17.62 mmol) in dry THF (90 ml) was slowly added a borane solution (1M in THF) (38.8 ml; 38.8 mmol) under nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 24 h. The reaction mixture was carefully quenched with a solution of sodium hydroxide 1N (40 ml), the organic volatiles were removed under reduced pressure and the remaining aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered and concentrated under reduced pressure to furnish 2.7 g (51%) of 8-bromo-4-(2-hydroxyethyl)-5-methoxyquinolin-2(1H)-one as a light brown solid.

Workup

  1. stirringstirred for 24 h
  2. customThe reaction mixture was carefully quenched with a solution of sodium hydroxide 1N (40 ml)
  3. customthe organic volatiles were removed under reduced pressure
  4. extractionthe remaining aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce3a7ec04c4e4a558194af3a8eb85027
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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