Hydrochloric Acid → 4-(6-methoxypyridin-3-yl)benzoic Acid

HRID 430897Notes

Reaction equation

HRID 430897 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:9][CH:8]=1)C.Cl>CO.C1COCC1>[CH3:20][O:19][C:16]1[N:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:21])=[O:5])=[CH:8][CH:9]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 186177044-(6-Methoxy-pyridin-3-yl)-benzoic acid ethyl ester

Product 1

HCID 46742594-(6-methoxypyridin-3-yl)benzoic AcidYield 93.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A 1N sodium hydroxide solution (20 mL) is added to a mixture of 4-(6-methoxy-pyridin-3-yl)-benzoic acid ethyl ester (2.43 g, 9.44 mmol) in MeOH (20 mL) and THF (20 mL) and stirred at 35° C. for 1 hour. The reaction is cooled and 1N HCl added until the pH is˜4. The precipitate is isolated by filtration and dried in a vacuum desiccator to give a the product as a white solid (2.03 g, 8.86 mmol). 1H NMR (DMSO-d6, 300 MHz) δ8.57 (d, 1H), 8.08 (dd, 1H), 7.99 (d, 2H), 7.82 (d, 2H), 6.95 (d, 1H), 3.89 (s, 3H).

Workup

  1. temperatureThe reaction is cooled
  2. customThe precipitate is isolated by filtration
  3. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-f9898765c411451f80c9db947ed80a40
Source dataset
uspto-grants-2001_11
Patent number
US06323227B1

Reaction notes

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