Methanol → 2-(4-Fluorophenoxy)-3-pyridinecarboxylic Acid Methyl Ester

HRID 844005Notes

Reaction equation

HRID 844005 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>>[CH3:23][O:14][C:13]([C:12]1[C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6051232-(4-Fluorophenoxy)nicotinic acid

Product 1

HCID 544371042-(4-Fluorophenoxy)-3-pyridinecarboxylic Acid Methyl EsterYield 64%

Procedure

A mixture of 20.0 g (89.6 mmol) of 2-(4-fluorophenoxy)-3-pyridinecarboxylic acid (for preparation, see: Villani, F. J. et al. J. Med. Chem., 1975, 18,3), 300 mL of methanol, and 5.5 mL of concentrated sulfuric acid was heated to reflux for 2 h. The cooled mixture was poured onto 500 mL of ice cold saturated aqueous sodium hydrogencarbonate solution, and the resulting precipitate was filtered, washed with water, and dreid under vacuum to give 12.9 g (64% yield) of the title compound as a white solid, mp 97-99° C. Anal. Calcd for C13H10NO3F: C, 63.16; H, 4.08; N, 5.67. Found: C, 62.80; H, 4.08; N, 5.50.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-2100a84577684974a80ea18588b6f1a7
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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