Hydrochloric Acid → 5-Fluoromethoxypyridine-2-carboxylic acid

HRID 1524633Notes

Reaction equation

HRID 1524633 reaction equation
[OH-].[Na+].[F:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=[O:13])=[N:10][CH:11]=1.Cl.[Na+].[Cl-]>C1COCC1.O.CCOC(C)=O.O>[F:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 57827265Methyl 5-fluoromethoxypyridine-2-carboxylate

Product 1

HCID 574758705-Fluoromethoxypyridine-2-carboxylic acidYield 48.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

N NaOH (81 μL) was added to a solution containing methyl 5-fluoromethoxypyridine-2-carboxylate (50 mg) in THF/water (2 mL, 3/1), and the mixture was stirred at RT for 10 min. Water (1 mL) was added to the reaction solution, followed by further stirring for 20 min. The reaction solution was made acidic with 5 N hydrochloric acid. EtOAc and a saturated NaCl solution were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration. The filtrate was concentrated to obtain the title compound (22.6 mg). 1H-NMR (CDCl3) δ (ppm): 5.81 (d, J=53.2 Hz, 2H), 7.61 (ddd, J=0.8, 2.8, 8.8 Hz, 1H), 8.25 (d, J=0.8, 8.8 Hz, 1H), 8.42 (d, J=2.4 Hz, 1H).

Workup

  1. stirringby further stirring for 20 min
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. customthe insoluble matter was separated by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b19bba0cd481476287e766aeb41c3580
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

Loading…