Hydrochloric Acid → 6-(4-fluorophenoxy)nicotinic acid

HRID 534728Notes

Reaction equation

HRID 534728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([O:17]CC)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23149051Ethyl 6-(4-fluorophenoxy)nicotinate

Product 1

HCID 167905786-(4-fluorophenoxy)nicotinic acidYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 6-[(4-fluorophenyl)oxy]-3-pyridinecarboxylate (D13) (0.275 g, 1.054 mmol) was taken up in 1,4-dioxane (5 mL) and lithium hydroxide (0.050 g, 2.109 mmol) was dissolved in water. The two solutions were combined and stirred at room temperature for 2 h. The mixture was acidified to pH 5 with 2M HCl and concentrated. The residue was taken up in ethyl acetate, dried and concentrated to yield the title compound as a cream/white solid (0.233 g). δH (DMSO-d6, 400 MHz) 13.20 (1H, bs), 8.65 (1H, dd), 8.28 (1H, dd), 7.26 (4H, m), 7.12 (1H, d). MS (ES): MH+ 234.2, (M-H+) 232.1.

Workup

  1. concentrationconcentrated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3457fef625624ad2b409a5bf996ed878
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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