Potassium Hydroxide → 2-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acid

HRID 446788Notes

Reaction equation

HRID 446788 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=1.[OH-].[K+]>CO.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58368005Ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

Product 1

HCID 145002352-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acidYield 102.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (20 g, 0.05 mol) in MeOH (200 mL), a solution of KOH (12.6 g, 0.22 mol) in water (50 mL) was added dropwise and the reaction mixture was stirred for 1 h at RT. The methanol was then removed and the reaction mixture was washed with EtOAc (2×100 mL) and acidified to pH˜3 with 1 N HCl at 0° C. The precipitated solid was then filtered and dried to afford 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (15 g, 92%) as a white solid.

Workup

  1. customThe methanol was then removed
  2. washthe reaction mixture was washed with EtOAc (2×100 mL)
  3. customacidified to pH˜3 with 1 N HCl at 0° C
  4. filtrationThe precipitated solid was then filtered
  5. customdried

Sources & evidence

ORD record
ord-a6441e39952b4f57b599434196c5cc2d
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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