Acetic Acid → [8-Chloro-2-methoxy-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid

HRID 1944309Notes

Reaction equation

HRID 1944309 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH3:31])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)=[CH:22][CH:21]=1)[C:10]([O:17][CH3:18])=[N:11]2.[OH-].[Na+].C(O)(=O)C>CO.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:32])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([O:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)=[CH:24][CH:25]=1)=[C:8]2[CH3:31]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67455341[8-Chloro-2-methoxy-4-methyl-3-(4-pyrazol-1-yl-benzyl)quinolin-5-yloxy]acetic acid methyl ester

Product 1

HCID 25096077[8-Chloro-2-methoxy-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acidYield 50.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of [8-chloro-2-methoxy-4-methyl-3-(4-pyrazol-1-yl-benzyl)quinolin-5-yloxy]acetic acid methyl ester (0.37 g) in methanol (7.0 mL) and water (0.7 mL) was treated with 5.0M aqueous sodium hydroxide solution (0.32 mL), and the resulting mixture was stirred at room temperature for 2 hours. The mixture was acidified by the addition of glacial acetic acid, diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and then concentrated under reduced pressure. The residue was crystallised from methanol to give title compound as a white solid (0.18 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallised from methanol

Sources & evidence

ORD record
ord-4650d15f612442619b4678eb15e90d36
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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