Potassium Iodide → (3-Iodo-quinolin-6-yloxy)-methoxy-acetic acid methyl ester

HRID 1962857Notes

Reaction equation

HRID 1962857 reaction equation
CC(C)([O-])C.[K+].[I:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([OH:18])=[CH:13][CH:12]=2.[CH3:19][O:20][C:21](=[O:26])[CH:22](Br)[O:23][CH3:24].[I-].[K+]>C(O)(C)(C)C.C(Cl)(Cl)Cl>[CH3:19][O:20][C:21](=[O:26])[CH:22]([O:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([I:7])=[CH:17]2)[O:23][CH3:24]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 12616599Methyl 2-bromo-2-methoxyacetateHCID 23665647Potassium tert-butoxideHCID 574180403-Iodoquinolin-6-ol

Product 1

HCID 59565406(3-Iodo-quinolin-6-yloxy)-methoxy-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6386tert-ButanolSolvent3×

Procedure

To a solution of potassium t-butoxide (1.36 g) in t-butyl alcohol (50 mL) was added a solution of 3-iodo-quinolin-6-ol (3 g) in t-butyl alcohol (5 mL). The reaction mixture was stirred at room temperature for 15 minutes. Bromo-methoxy-acetic acid methyl ester (4.0 g) and a solution of potassium iodide (catalytic quantity) in t-butyl alcohol (5 mL) were then added. The reaction mixture was stirred at room temperature for 18 hours. The mixture was poured on water and chloroform was added. The mixture was stirred. The two layers were separated, the aqueous layer was extracted with chloroform (twice). The organic layers were combined, washed with brine (twice), dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude (4.3 g) was used directly in the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. additionwas added
  3. stirringThe mixture was stirred
  4. customThe two layers were separated
  5. extractionthe aqueous layer was extracted with chloroform (twice)
  6. washwashed with brine (twice),
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude (4.3 g) was used directly in the next step without purification

Sources & evidence

ORD record
ord-0e531a1030cc4b34ba9224bd6e9e9e03
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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