Hydrochloric Acid → 4-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]quinolin-7-yloxy)-butyric acid

HRID 867479

Reaction equation

HRID 867479 reaction equation
[O:1]=[C:2]1[NH:22][C:5]2=[N:6][C:7]3[CH:8]=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:11][C:12]=3[CH:13]=[C:4]2[NH:3]1.Cl>CO>[O:1]=[C:2]1[NH:22][C:5]2=[N:6][C:7]3[CH:8]=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][C:12]=3[CH:13]=[C:4]2[NH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10017729HCID 10017729, compound

Product 1

HCID 142809904-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]quinolin-7-yloxy)-butyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)oxy]butanoate (1.0 g, 3.3 mmol) was added to a solution of 50% aqueous methanol containing 4N NaOH (2 mL). After stirring for 1 hour, the mixture was acidified to pH=3 by the addition of 2N HCl. The precipitate was washed with water, methanol and diethyl ether to give 4-[(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)oxy]butyric acid as a partial hydrate (0.84 g, 88%). An analytical sample was prepared by crystalization from dimethylformamide/H2O and had m.p.>320°.

Workup

  1. washThe precipitate was washed with water, methanol and diethyl ether

Sources & evidence

ORD record
ord-8df33cc007ce4e258390f5b7634aa8db
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Linked notes

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