1,5-Dibromopentane → HCID 67301381, compound

HRID 1015423Notes

Reaction equation

HRID 1015423 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 135441757Quinolin-5-ol

Product 1

HCID 67301381HCID 67301381, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 5-hydroxyquinoline (10.0 g, 69.0 mmol) and 1,5-dibromo-pentane (23.9 g, 103.5 mmol) in N-methylpyrrolidinone (100 mL) was added potassium carbonate (14.7 g, 103.5 mmol). The resulting mixture was stirred at 90° C. for 4 h and then quenched with water (30 mL) followed by extraction with ethyl acetate (30 mL×3). The organic layers were combined, washed with brine, and then concentrated under vacuum. The residue was purified by silica gel chromatography to give 5-(5-bromo-pentyloxy)-quinoline (12.6 g, 42.8 mmol, 62%) as a white solid.

Workup

  1. customquenched with water (30 mL)
  2. extractionfollowed by extraction with ethyl acetate (30 mL×3)
  3. washwashed with brine
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-887c4201682b4acc964310b63d2b4dea
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

Loading…