Potassium Hydroxide → HCID 86732805, compound

HRID 525937Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:33])[C:9]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]=2)[C:6](=[O:34])[C:5]([C:35]([O:37]CC2C=CC(OC)=CC=2)=[O:36])=[CH:4]1)[CH3:2].[OH-].[K+]>CO.O>[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:33])[C:9]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[C:10]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH:11]=2)[C:6](=[O:34])[C:5]([C:35]([OH:37])=[O:36])=[CH:4]1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 4-methoxybenzyl 1-ethyl-5-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (68 g, 108 mmol) in a mixture of Methanol (250 mL) and Water (125 mL) was added KOH (12.16 g, 217 mmol) portionwise. The resulting mixture was stirred at 90° C. for 3 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 6 N HCl (aq.). The precipitates were collected by filtration and dried to afford 1-ethyl-5-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (50 g, 99 mmol, 91% yield) as a brown solid. LCMS: (M+H)+: 508.2.

Workup

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

Sources & evidence

ORD record: ord-7c588db761004834882752a6e8d67639
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340556B2

Reaction notes

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