Potassium Hydroxide → HCID 86732832, compound

HRID 525968Notes

Reaction equation

HRID 525968 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[C:11]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH:12]=3)[C:7](=[O:34])[C:6]([C:35]([O:37]CC3C=CC(OC)=CC=3)=[O:36])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[K+]>CO.O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([O:24][CH2:25][C:26]4[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)=[C:11]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)[CH:12]=3)[C:7](=[O:34])[C:6]([C:35]([OH:37])=[O:36])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86732833HCID 86732833, compound

Product 1

HCID 86732832HCID 86732832, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-methoxybenzyl 1-cyclopropyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (14 g, 22.52 mmol) in a mixture of Methanol (100 mL) and Water (50.0 mL) was added KOH (2.53 g, 45.0 mmol) portionwise. The resulting mixture was stirred at 90° C. for 2 h. LCMS indicated completion of the reaction. The reaction mixture was cooled down to r.t. and concentrated, and was then diluted with water and adjusted pH to 1 using 2 N HCl (aq.). The precipitates were collected by filtration and dried to afford 1-cyclopropyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (11 g, 21.93 mmol, 97% yield) as pale yellow solid. LCMS: [M+H]+: 502.3.

Workup

  1. customcompletion of the reaction
  2. temperatureThe reaction mixture was cooled down to r.t.
  3. concentrationconcentrated
  4. additionwas then diluted with water and adjusted pH to 1 using 2 N HCl (aq.)
  5. filtrationThe precipitates were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ec7fd03b727c4f559490c9849f79a93d
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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