Hydrochloric Acid → 3-(6-Methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester

HRID 215829

Reaction equation

HRID 215829 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[OH:10][C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+].Cl>N1C=CC=CC=1.[Cu]I>[CH2:17]([O:16][C:14](=[O:15])[C:13]1[CH:19]=[CH:20][CH:21]=[C:11]([O:10][C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[CH:12]=1)[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoateHCID 27348955-Bromo-2-methoxypyridine

Product 1

HCID 672971443-(6-Methoxy-pyridin-3-yloxy)-benzoic acid ethyl esterYield 23.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolvent

Procedure

A suspension of 5-bromo-2-methoxy-pyridine (5.4 g, 29 mmol), ethyl 3-hydroxybenzoate (4.0 g, 24 mmol), K2CO3 (4.3 g, 30 mmol), Cu powder (0.30 g, 4.8 mmol) and CuI (0.30 g, 1.56 mmol) in pyridine (25 ml) was refluxed for 18 h. The resulting mixture was mixed with 100 g of crushed ice, neutralized with 1N hydrochloric acid to pH 7.5 and extracted with ether. The extract was evaporated in vacuo, the obtained crude product was purified by column chromatography on silica (eluent hexanes-ethyl acetate 8:1) to afford 1.55 g (20%) of 3-(6-methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester as colorless oil.

Workup

  1. temperaturewas refluxed for 18 h
  2. extractionextracted with ether
  3. customThe extract was evaporated in vacuo
  4. customthe obtained crude product
  5. customwas purified by column chromatography on silica (eluent hexanes-ethyl acetate 8:1)

Sources & evidence

ORD record
ord-44adbd6a96364be3b0f83d8ea7a0810e
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Linked notes

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