Hydrochloric Acid → 2-(3-Chloro-4-(quinolin-2-ylmethoxy)phenyl)acetic acid

HRID 446827Notes

Reaction equation

HRID 446827 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([O:23]CC)=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.CO.O[Li].O.Cl>O.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([OH:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 67075604Ethyl 2-(3-chloro-4-(quinolin-2-ylmethoxy)phenyl)acetate

Product 1

HCID 190877742-(3-Chloro-4-(quinolin-2-ylmethoxy)phenyl)acetic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(3-chloro-4-(quinolin-2-ylmethoxy)phenyl)acetate (1.0 g, 0.02 mol) in 1:1 MeOH:THF (20 mL) was added LiOH.H2O (1.76 g, 0.008 mol). The reaction mixture was then stirred at RT for 16 h and then concentrated in vacuo to obtain the crude product. The crude material was diluted with water and adjusted to pH 4 using 1N HCl. The mixture was then filtered and the residue was dried in vacuo to afford 2-(3-chloro-4-(quinolin-2-ylmethoxy)phenyl)acetic acid (800 mg, 86%) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain the crude product
  3. filtrationThe mixture was then filtered
  4. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-3c837bcb530145ff88ae433498043fd7
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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