Hydrochloric Acid → 2-Fluoro-2-(quinolin-6-yl)acetic acid

HRID 40249Notes

Reaction equation

HRID 40249 reaction equation
[F:1][CH:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)[C:3]([O:5]C)=[O:4].[OH-].[Na+].Cl>CO>[F:1][CH:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57691374Methyl 2-fluoro-2-(quinolin-6-yl)acetate

Product 1

HCID 576909192-Fluoro-2-(quinolin-6-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing methyl 2-fluoro-2-(quinolin-6-yl)acetate (0.49 g, 2.2 mmol) in methanol (3.0 ml) was added sodium hydroxide (5 M, 1.0 ml, 5.0 mmol). The mixture was stirred at rt for 48 h and then neutralized with 5 N HCl (1.0 mL). The solution was allowed to sit overnight during which time a precipitate formed. The solution was filtered and the filtercake washed with cold water then dried under vacuum to afford the title compound as a tan solid. MS (ESI, pos. ion) m/z: 206 (M+1).

Workup

  1. waitto sit overnight during which time
  2. customa precipitate formed
  3. filtrationThe solution was filtered
  4. washthe filtercake washed with cold water
  5. customthen dried under vacuum

Sources & evidence

ORD record
ord-26ae624a25a94630a06b4ca858f39aa0
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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