Boron tribromide → 7-Hydroxy-3,4-dihydrocarbostyril

HRID 490695Notes

Reaction equation

HRID 490695 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 27857587-Hydroxy-3,4-dihydrocarbostyrilYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-methoxy-3,4-dihydro-1H-quinolin-2-one (1.30 g, 7.34 mmol) in CH2Cl2 (100 mL) at 0° C. is treated with BBr3 (14.7 mL, 1.0 M in CH2Cl2) added dropwise. The mixture is stirred for 48 hours at room temperature and then quenched with water dropwise. The suspension is filtered and the solid is rinsed with MeOH (2 mL) and dried under vacuum to obtain the product (0.90 g, 75%).

Workup

  1. additionadded dropwise
  2. customquenched with water dropwise
  3. filtrationThe suspension is filtered
  4. washthe solid is rinsed with MeOH (2 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3a38fa6ac64a4b7abb62923067525963
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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