2-Hydroxyquinoline → 6-Bromoquinolin-2(1H)-one

HRID 1732191Notes

Reaction equation

HRID 1732191 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]1=[O:3].[Br:12]Br>C(O)(=O)C>[Br:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[NH:1][C:2](=[O:3])[CH:4]=[CH:5]2

Participants

4

Reactant 2

HCID 60382-Hydroxyquinoline2×HCID 24408Bromine

Product 1

HCID 123789436-Bromoquinolin-2(1H)-oneYield 48.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
38 °C

Procedure

0.07 Mols (10.16 g) of carbostyril were put into 100 ml acetic acid in a 500 ml round bottom flask fitted with an air stirrer, thermometer and a vented dropping funnel. It was stirred and warmed to 56° C. where the carbostyril was in solution. 0.075 Mols (12.0 g) of bromine were put into 50 ml of acetic acid and added to the reaction over a one hour period. The temperature was held between 56° and 65° C. The reaction was then stirred for 13/4 hr. at 63°-65° C. It was then cooled to 38° C. and the solids filtered off. From this and the filtrate were obtained 7.65 g of 6-bromocarbostyril (product checked by IR). A second fraction of 3.9 g was also obtained which looked to be a mixture of monobromo and dibromocarbostyril.

Workup

  1. customfitted with an air stirrer
  2. additionadded to the reaction over a one hour period
  3. customwas held between 56° and 65° C
  4. stirringThe reaction was then stirred for 13/4 hr
  5. customat 63°-65° C
  6. filtrationthe solids filtered off

Sources & evidence

ORD record
ord-6955c9b657c34d1e86e7de3522383b44
Source dataset
uspto-grants-1980_12
Patent number
US04236912

Reaction notes

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