Hydrochloric Acid → {4-Chloro-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetic acid

HRID 2390331Notes

Reaction equation

HRID 2390331 reaction equation
C([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24])(C)(C)C.Cl>C(Cl)Cl>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:25])=[O:5])=[C:10]([C:16]#[C:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[CH3:24])[CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58521948Tert-butyl{4-chloro-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetate2×

Product 1

HCID 56594387{4-Chloro-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl{4-chloro-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetate (Intermediate 19, 138 mg; 0.39 mmol) in DCM (1.4 mL) was treated with an HCl solution (4 N in dioxane, 2.7 mL). After stirring for 20 hours, the solvents were removed under vacuum to afford the title compound as a beige solid (107 mg, 82%).

Workup

  1. customthe solvents were removed under vacuum

Sources & evidence

ORD record
ord-1693fac18921414eaad4aaffa2a67219
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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