Potassium Hydroxide → 1-Ethyl-5-hydroxy-6-((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 525961Notes

Reaction equation

HRID 525961 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([OH:23])[C:9]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:10][CH:11]=2)[C:6](=[O:24])[C:5]([C:25]([O:27]CC)=[O:26])=[CH:4]1)[CH3:2].[OH-].[K+]>CO.O>[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([OH:23])[C:9]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:10][CH:11]=2)[C:6](=[O:24])[C:5]([C:25]([OH:27])=[O:26])=[CH:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86732827Ethyl 1-ethyl-5-hydroxy-6-((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 867328281-Ethyl-5-hydroxy-6-((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of ethyl 1-ethyl-5-hydroxy-6-((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (1.5 g, 3.77 mmol) in a mixture of Methanol (60.0 mL) and Water (20 mL) was added KOH (0.424 g, 7.55 mmol) portionwise. The resulting mixture was stirred under reflux for 1 h. The mixture was cooled down to r.t. and concentrated. Water was added and the mixture was adjusted to pH˜2 using 6 N HCl (aq.). The precipitates were collected by filtration and dried in air to afford 1-ethyl-5-hydroxy-6-((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1.35 g, 3.65 mmol, 97% yield) as a light yellow solid. LCMS: (M+H)+: 370.2.

Workup

  1. temperatureunder reflux for 1 h
  2. concentrationconcentrated
  3. additionWater was added
  4. filtrationThe precipitates were collected by filtration
  5. customdried in air

Sources & evidence

ORD record
ord-d167a72b352a474dab17a6fd90823244
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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