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

HRID 1504199Notes

Reaction equation

HRID 1504199 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. Methanol 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-160b2d7e4ecc423f976ea6c51d571da5
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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