Hydrochloric Acid → HCID 53384862, compound

HRID 588075Notes

Reaction equation

HRID 588075 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:7][N:6]=1)=[O:4].O.[Li+].[OH-].Cl>C1COCC1>[F:19][C:15]1[CH:14]=[C:13]([C:12]#[C:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 90103011HCID 90103011, compound

Product 1

HCID 53384862HCID 53384862, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1.9 g, 7.44 mmol) 5-(3-Fluoro-phenylethynyl)-pyridine-2-carboxylic acid methyl ester (Example 1, step 1) was dissolved in THF (30 ml) and water (30 ml) and LiOH (357 mg, 24.9 mmol, 2 equiv.) was added at room temperature. The mixture was stirred for 16 hours at room temperature. The reaction mixture was acidified with 4N HCl to pH 2.5 and THF was evaporated to form a yellow suspension. The suspension was cooled to 0-5° C. and filtered. The crystals were washed with cold water and evaporated to dryness. The desired 5-(3-fluoro-phenylethynyl)-pyridine-2-carboxylic acid (1.71 g, 95% yield) was obtained as a light yellow solid, MS: m/e=239.9 (M+H+).

Workup

  1. customwas evaporated
  2. customto form a yellow suspension
  3. temperatureThe suspension was cooled to 0-5° C.
  4. filtrationfiltered
  5. washThe crystals were washed with cold water
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-27f67db9e652408f9169b21fb39fb101
Source dataset
uspto-grants-2016_01
Patent number
US09227959B2

Reaction notes

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