Potassium Hydroxide → HCID 86732756, compound

HRID 525891Notes

Reaction equation

HRID 525891 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:11]=2[F:13])[C:6](=[O:34])[C:5]([C:35]([O:37]CC)=[O:36])=[CH:4]1)[CH3:2].[OH-].[K+]>CO.O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)=[C:10]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[C:11]=2[F:13])[C:6](=[O:34])[C:5]([C:35]([OH:37])=[O:36])=[CH:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86732757HCID 86732757, compound

Product 1

HCID 86732756HCID 86732756, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of ethyl 1-ethyl-8-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (32 g, 59.8 mmol) in a mixture of Methanol (250 mL) and Water (125 mL) was added KOH (6.70 g, 120 mmol) portionwise. The resulting mixture was stirred at 90° C. for 3 h. LCMS indicated completion of the reaction. The mixture was cooled down to r.t. and concentrated. Water was then added, and the mixture was adjusted to pH ˜1 using 6 N aq. HCl. The precipitate was collected by filtration and dried to afford 1-ethyl-8-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (28 g, 55.2 mmol, 92% yield) as a yellow solid. LCMS (M+H)+: 508.2.

Workup

  1. customcompletion of the reaction
  2. temperatureThe mixture was cooled down to r.t.
  3. concentrationconcentrated
  4. additionWater was then added
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-8ca7b8714ec5426ab9a3e1dd9dc6eb1b
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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