Potassium Hydroxide → HCID 86732764, compound

HRID 525901Notes

Reaction equation

HRID 525901 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:46])[C:5]([C:34]([O:36]CC1C=CC(OC)=CC=1)=[O:35])=[CH:6][N:7]2[CH2:32][CH3:33].[OH-].[K+]>CO.O>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:46])[C:5]([C:34]([OH:36])=[O:35])=[CH:6][N:7]2[CH2:32][CH3:33]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86732763HCID 86732763, compound

Product 1

HCID 86732764HCID 86732764, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-methoxybenzyl 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (8.4 g, 13.04 mmol) in a mixture of Methanol (90 mL) and Water (30.0 mL) was added KOH (1.463 g, 26.1 mmol) portionwise. The resulting mixture was stirred under reflux for 1.5 h. The mixture was then cooled down to r.t., concentrated, diluted with water (150 mL) and adjusted pH to 2-3 using 6 N HCl (aq.). The precipitates were collected by filtration and dried to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (6.7 g, 12.79 mmol, 98% yield) as a white solid. LCMS: (M+H)+: 524.2.

Workup

  1. temperatureunder reflux for 1.5 h
  2. concentrationconcentrated
  3. additiondiluted with water (150 mL)
  4. filtrationThe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-047b5eeee8d14b7eaba64cad313b241f
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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