1,5-Dibromopentane → HCID 54274067, compound

HRID 328045Notes

Reaction equation

HRID 328045 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:12]([OH:22])[CH:11]=[CH:10][C:9]=2[N:8]=1)[CH3:2].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30].C(=O)([O-])[O-].[K+].[K+].O.[C:38]1(C)C=CC(S(O)(=O)=O)=C[CH:39]=1>CC(=O)CC>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH2:17][CH2:18][C:19]([O:21][CH2:38][CH3:39])=[O:20])=[C:12]([O:22][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30])[CH:11]=[CH:10][C:9]=2[N:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 53904548HCID 53904548, compound

Product 1

HCID 54274067HCID 54274067, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.866 g (2.51 mmol) of 6-hydroxy-2,5quinolinedipropanoic acid ethyl ester from the preceding example, 2.33 g (10.1 mmol) of 1,5-dibromopentane, 1.75 g (12.7 mmol) of anhydrous granular potassium carbonate and 25 mL of 2-butanone was stirred at 90° C. for 8.25 hr and at room temperature for another 37 hr. The mixture was filtered through anhydrous magnesium sulfate and the solids were washed with ethyl acetate. The filtrate and washes were combined and concentrated under reduced pressure. The residue was dissolved in 200 mL of ethanol, 1.21 g (6.36 mmol) of p-toluenesulfonic acid monohydrate was added and the resulting solution was stirred at room temperature for 22 hr. Most the ethanol was removed under reduced pressure. The residue was treated with saturated aqueous sodium bicarbonate and worked-up with ethyl acetate in the usual manner. The crude product was partially purified by flash chromatography on 110 g of silica gel, eluting with hexane-ethyl acetate (3:1 and 2:1) giving 1.03 g of the title compound.

Workup

  1. filtrationThe mixture was filtered through anhydrous magnesium sulfate
  2. washthe solids were washed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in 200 mL of ethanol
  5. stirringthe resulting solution was stirred at room temperature for 22 hr
  6. customMost the ethanol was removed under reduced pressure
  7. additionThe residue was treated with saturated aqueous sodium bicarbonate
  8. customThe crude product was partially purified by flash chromatography on 110 g of silica gel
  9. washeluting with hexane-ethyl acetate (3:1 and 2:1)

Sources & evidence

ORD record
ord-c54d8eeafcbe4af19692d448db924d54
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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