Lithium Hydroxide → 2-(3-(3-Hexylquinoline-8-carboxamido)phenoxy)acetic acid

HRID 472793Notes

Reaction equation

HRID 472793 reaction equation
[OH-].[Li+].[CH2:3]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][CH2:26][C:27]([O:29]C(C)C)=[O:28])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>O>[CH2:3]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][CH2:26][C:27]([OH:29])=[O:28])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66660805Isopropyl 2-(3-(3-hexylquinoline-8-carboxamido)phenoxy)acetate

Product 1

HCID 565964142-(3-(3-Hexylquinoline-8-carboxamido)phenoxy)acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous 2 N lithium hydroxide (0.7 mL, 1.4 mmol) and water (0.7 mL) were added to a solution of isopropyl 2-(3-(3-hexylquinoline-8-carboxamido)phenoxy)acetate (210 mg, 0.47 mmol) in THE (5.0 mL) and the solution was stirred at room temperature. After 20 h, the THF was removed in vacuo. The residual aqueous phase was adjusted to pH 4-5 with 1 N aqueous HCl and extracted with EtOAc (3×). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford 177 mg (93%) of the title compound.

Workup

  1. customthe THF was removed in vacuo
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b996075c65e44fd59926d12df1db2e38
Source dataset
uspto-grants-2014_01
Patent number
US08633220B2

Reaction notes

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