Hydrochloric Acid → 4-[2-(3,5-Dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylic acid

HRID 1937423Notes

Reaction equation

HRID 1937423 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]([C:11]1[C:16]2[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[O:19][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10].[OH-].[Na+].Cl>CO>[Cl:27][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]([C:11]1[C:16]2[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[O:19][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22733875Ethyl 4-[2-(3,5-dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylate

Product 1

HCID 227341684-[2-(3,5-Dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-[2-(3,5-dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylate (6.0 g) was dissolved in methanol (60 ml), 5 N aqueous NaOH (15 ml) was added thereto under cooling on ice, and the mixture was returned to room temperature and stirred for 1 hour. Under cooling on ice, the reaction mixture was acidified by dropwise adding 1 N aqueous HCl, and the precipitated crystals were collected by filtration and washed with water to give the desired compound (5.4 g, 96%) as colorless crystals.

Workup

  1. temperatureunder cooling on ice
  2. customwas returned to room temperature
  3. temperatureUnder cooling on ice
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-b54a1c71068a479791f8647616bab739
Source dataset
uspto-grants-2002_05
Patent number
US06395738B1

Reaction notes

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