Hydrochloric Acid → {N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)amino}acetic acid

HRID 69028Notes

Reaction equation

HRID 69028 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:32])[CH2:7][N:8]([CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:30])[C:25](=[O:31])[CH:24]=[CH:23]2)[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)C.Cl>CO>[CH3:30][N:26]1[C:27]2[C:22](=[CH:21][C:20]([O:19][CH2:18][CH2:17][CH2:16][N:8]([CH2:7][C:6]([OH:32])=[O:5])[CH2:9][C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[CH:29][CH:28]=2)[CH:23]=[CH:24][C:25]1=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86762688{N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)amino}acetic acid ethyl ester

Product 1

HCID 86762696{N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)amino}acetic acidYield 81.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 1N-sodium hydroxide aqueous solution (3 ml) was added to a methanol solution (15 ml) of {N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)amino}acetic acid ethyl ester (614 mg). The mixture was stirred at room temperature overnight. 1N-Hydrochloric acid (3 ml) was added to the reaction mixture and condensed under reduced pressure. Metanol was added to the residue, and the generated insoluble matter was separated by filtration. The filtrate was condensed under reduced pressure to give the title compound (468 mg) as a white amorphous solid.

Workup

  1. customthe generated insoluble matter was separated by filtration
  2. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-2c1fced50ff343d3b9d05e4e5333829e
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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