Hydrochloric Acid → 2-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acid

HRID 446798Notes

Reaction equation

HRID 446798 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.C1COCC1.O[Li].O.Cl>CO>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 58368005Ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

Product 1

HCID 145002352-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acidYield 119.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (8 g, 0.02 mol) in MeOH:THF (300 mL; 1:1) was added LiOH.H2O (5.21 g, 0.124 mol). The reaction mixture was stirred at RT for 1 h and then concentrated in vacuo to obtain the crude compound. The crude material was acidified with HCl (1N), filtered and dried in vacuo to afford 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (7.0 g, 95%) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain the crude compound
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-56f2a63e60e049e58cb8c4d4292c3fbe
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

Loading…