Broxyquinoline → HCID 11186570, compound

HRID 1371256Notes

Reaction equation

HRID 1371256 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([Br:12])[C:9](O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Br[CH2:15][CH2:16][OH:17].CN(C)C=O>O>[Br:1][C:2]1[CH:11]=[C:10]([Br:12])[C:9]([CH2:15][CH2:16][OH:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 2453BroxyquinolineHCID 6228DimethylformamideHCID 108982-Bromoethanol3×

Product 1

HCID 11186570HCID 11186570, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3.79 g of 5,7-dibromo-8-hydroxyquinoline (12.5 mmol) and 975 mL of 2-bromoethanol (13.75 mmol) in 20 mL of dry dimethylformamide containing 5.18 g anhydrous potassium carbonate (37.5 mmol) was placed under argon atmosphere and heated at 60° C. with vigorous magnetic stirring. After 4 hr a further 220 μL of 2-bromoethanol was added and stirring continued at 60° overnight. After 22 hr another 440 μL of 2-bromoethanol was added. After 4 days the mixture was poured into 150 mL of water while stirring. The precipitated product was collected by filtration, washed with 50 mL of 0.5 M aqueous potassium carbonate, plain water and air dried. The solid was washed through the funnel by dissolving in dichloromethane, and the solvent was removed to yield 3.18 g of 5,7-dibromo-8-(2-hydroxyethyl)quinoline. After recrystallization from methanol/water containing a little triethylamine, the melting point was 128–131° C.

Workup

  1. stirringwhile stirring
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with 50 mL of 0.5 M aqueous potassium carbonate, plain water and air
  4. customdried
  5. washThe solid was washed through the funnel
  6. dissolutionby dissolving in dichloromethane
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-52f211993ca149568dcb695dfebbb221
Source dataset
uspto-grants-2007_01
Patent number
US07157408B2

Reaction notes

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