Hydrochloric Acid → 7-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid

HRID 1635121Notes

Reaction equation

HRID 1635121 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:23])[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:9]=2[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:4].[OH-].[Na+].Cl>CO.O>[CH3:16][O:15][C:10]1[C:9]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:8]2[C:13]([CH:14]=[C:5]([C:3]([OH:4])=[O:2])[C:6](=[O:23])[NH:7]2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98618427-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid methyl ester

Product 1

HCID 99045957-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid methyl ester (240 mg) obtained in Example 1-1 was dissolved in methanol (7 ml) and water (3 ml), to which sodium hydroxide (120 ml) was added, and the solution was stirred at room temperature for 1.5 hours. While the reaction vessel was cooled with ice, the solution was acidified with the addition of concentrated hydrochloric acid, and extracted with ethyl acetate (20 ml). The organic layer was dried over anhydrous sodium sulfate, filtered to remove the desiccating agent, and concentrated under reduced pressure to give the title compound (228 ml) (Table 6).

Workup

  1. temperatureWhile the reaction vessel was cooled with ice
  2. extractionextracted with ethyl acetate (20 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customto remove the desiccating agent
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77cc9f170bbe40c6bf4fdcba4bc53428
Source dataset
uspto-grants-2003_01
Patent number
US06509352B1

Reaction notes

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