Hydrochloric Acid → 6-(cyclopropylmethoxy)-5-fluoronicotinic Acid

HRID 2277169Notes

Reaction equation

HRID 2277169 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:15]([F:16])=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][N:7]=2)[CH2:3][CH2:2]1.C1COCC1.[OH-].[Li+].Cl>CO>[CH:1]1([CH2:4][O:5][C:6]2[C:15]([F:16])=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86731223Methyl 6-(cyclopropylmethoxy)-5-fluoronicotinate

Product 1

HCID 867312246-(cyclopropylmethoxy)-5-fluoronicotinic AcidYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 6-(cyclopropylmethoxy)-5-fluoronicotinate (1.75 g), THF (15 mL), methanol (1.7 mL) and 2 M aqueous lithium hydroxide solution (7.8 mL) was stirred at room temperature for 20 min. The reaction mixture was neutralized with 1 M hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure, and the obtained solid was washed with diethyl ether to give the title compound (1.21 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washthe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-407e9b535923409daa368142e67a889d
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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