Hydrochloric Acid → HCID 86731368, compound

HRID 2277286Notes

Reaction equation

HRID 2277286 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].F[C:9]1[CH:17]=[C:16]([CH3:18])[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1.Cl>C1COCC1>[CH:1]1([CH2:4][O:5][C:9]2[CH:17]=[C:16]([CH3:18])[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 467392746-Fluoro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 86731368HCID 86731368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylmethanol (3.92 mL) was added to a suspension of sodium hydride (60% oil, 1.93 g) in THF (30 mL) by small portions at 0° C., and the obtained mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 6-fluoro-4-methylnicotinic acid, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was recrystallized (hexane/ethyl acetate) to give the title compound (1.14 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained solid was recrystallized (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d2ed649047164c8eb647988cb572aadc
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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